Improved syntheses of d-ribo- and 2-deoxy-d-ribofuranose phospho sugars from methyl β-d-ribopyranoside

Tadashi Hanaya; Yuko Koga; Heizan Kawamoto; Hiroshi Yamamoto

doi:10.3987/COM-07-S(U)34

Improved syntheses of d-ribo- and 2-deoxy-d-ribofuranose phospho sugars from methyl β-d-ribopyranoside

Tadashi Hanaya, Yuko Koga, Heizan Kawamoto, Hiroshi Yamamoto

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Abstract

Abstract - Methyl 4-deoxy-4-dimethoxyphosphinoyl-2,3-O-isopropylidene-13-D-ribopyranoside (12a) and methyl 2,4-dideoxy-4-dimethoxyphosphinoyl-13-D-etythro-pentopyranoside (20) were efficiently prepared respectively from methyl2,3-O-isopropylidene-[3-D-ribopyranoside (7a) and its 3,4-O-isopropylideneisomer (7b) in appreciably improved total yields compared with those via previously reported routes.Compounds (12a, 20) were led to D-ribofuranos and 2-deoxy-D-ribofuranose phospho sugars (4, 5).

Original language	English
Pages (from-to)	581-591
Number of pages	11
Journal	Heterocycles
Volume	73
Issue number	C
DOIs	https://doi.org/10.3987/COM-07-S(U)34
Publication status	Published - 2007

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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title = "Improved syntheses of d-ribo- and 2-deoxy-d-ribofuranose phospho sugars from methyl β-d-ribopyranoside",

abstract = "Abstract - Methyl 4-deoxy-4-dimethoxyphosphinoyl-2,3-O-isopropylidene-13-D-ribopyranoside (12a) and methyl 2,4-dideoxy-4-dimethoxyphosphinoyl-13-D-etythro-pentopyranoside (20) were efficiently prepared respectively from methyl2,3-O-isopropylidene-[3-D-ribopyranoside (7a) and its 3,4-O-isopropylideneisomer (7b) in appreciably improved total yields compared with those via previously reported routes.Compounds (12a, 20) were led to D-ribofuranos and 2-deoxy-D-ribofuranose phospho sugars (4, 5).",

author = "Tadashi Hanaya and Yuko Koga and Heizan Kawamoto and Hiroshi Yamamoto",

year = "2007",

doi = "10.3987/COM-07-S(U)34",

language = "English",

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pages = "581--591",

journal = "Heterocycles",

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publisher = "Japan Institute of Heterocyclic Chemistry",

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TY - JOUR

T1 - Improved syntheses of d-ribo- and 2-deoxy-d-ribofuranose phospho sugars from methyl β-d-ribopyranoside

AU - Hanaya, Tadashi

AU - Koga, Yuko

AU - Kawamoto, Heizan

AU - Yamamoto, Hiroshi

PY - 2007

Y1 - 2007

N2 - Abstract - Methyl 4-deoxy-4-dimethoxyphosphinoyl-2,3-O-isopropylidene-13-D-ribopyranoside (12a) and methyl 2,4-dideoxy-4-dimethoxyphosphinoyl-13-D-etythro-pentopyranoside (20) were efficiently prepared respectively from methyl2,3-O-isopropylidene-[3-D-ribopyranoside (7a) and its 3,4-O-isopropylideneisomer (7b) in appreciably improved total yields compared with those via previously reported routes.Compounds (12a, 20) were led to D-ribofuranos and 2-deoxy-D-ribofuranose phospho sugars (4, 5).

AB - Abstract - Methyl 4-deoxy-4-dimethoxyphosphinoyl-2,3-O-isopropylidene-13-D-ribopyranoside (12a) and methyl 2,4-dideoxy-4-dimethoxyphosphinoyl-13-D-etythro-pentopyranoside (20) were efficiently prepared respectively from methyl2,3-O-isopropylidene-[3-D-ribopyranoside (7a) and its 3,4-O-isopropylideneisomer (7b) in appreciably improved total yields compared with those via previously reported routes.Compounds (12a, 20) were led to D-ribofuranos and 2-deoxy-D-ribofuranose phospho sugars (4, 5).

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VL - 73

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JO - Heterocycles

JF - Heterocycles

SN - 0385-5414

IS - C

ER -

Improved syntheses of d-ribo- and 2-deoxy-d-ribofuranose phospho sugars from methyl β-d-ribopyranoside

Abstract

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