(2S,3S)-3-O-[2',6'-di-O-benzyl-3',4'-di-O-(2,3-dimethoxybutane-2,3-diyl)-α-D-glucopyranosyl]-1,2-O-isopropylidene-5-O-tert-butyldiphenylsilyl-α-D-ribofuranoside

Base Information

Chemical Name:(2S,3S)-3-O-[2',6'-di-O-benzyl-3',4'-di-O-(2,3-dimethoxybutane-2,3-diyl)-α-D-glucopyranosyl]-1,2-O-isopropylidene-5-O-tert-butyldiphenylsilyl-α-D-ribofuranoside
CAS No.:197644-81-8
Molecular Formula:C₅₀H₆₄O₁₂Si
Molecular Weight:885.136
Hs Code.:

(2S,3S)-3-O-[2',6'-di-O-benzyl-3',4'-di-O-(2,3-dimethoxybutane-2,3-diyl)-α-D-glucopyranosyl]-1,2-O-isopropylidene-5-O-tert-butyldiphenylsilyl-α-D-ribofuranoside

Synonyms:(2S,3S)-3-O-[2',6'-di-O-benzyl-3',4'-di-O-(2,3-dimethoxybutane-2,3-diyl)-α-D-glucopyranosyl]-1,2-O-isopropylidene-5-O-tert-butyldiphenylsilyl-α-D-ribofuranoside

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Chemical Property of (2S,3S)-3-O-[2',6'-di-O-benzyl-3',4'-di-O-(2,3-dimethoxybutane-2,3-diyl)-α-D-glucopyranosyl]-1,2-O-isopropylidene-5-O-tert-butyldiphenylsilyl-α-D-ribofuranoside

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Technology Process of (2S,3S)-3-O-[2',6'-di-O-benzyl-3',4'-di-O-(2,3-dimethoxybutane-2,3-diyl)-α-D-glucopyranosyl]-1,2-O-isopropylidene-5-O-tert-butyldiphenylsilyl-α-D-ribofuranoside

There total 4 articles about (2S,3S)-3-O-[2',6'-di-O-benzyl-3',4'-di-O-(2,3-dimethoxybutane-2,3-diyl)-α-D-glucopyranosyl]-1,2-O-isopropylidene-5-O-tert-butyldiphenylsilyl-α-D-ribofuranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

: 190970-10-6
1,2-O-isopropylidene-5-O-tert-butyldiphenylsilyl-α-D-ribofuranose

: 197644-80-7
(2'S,3'S)-ethyl 2,6-di-O-benzyl-3,4-di-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-β-D-glucopyranoside

: 197644-81-8
(2S,3S)-3-O-[2',6'-di-O-benzyl-3',4'-di-O-(2,3-dimethoxybutane-2,3-diyl)-α-D-glucopyranosyl]-1,2-O-isopropylidene-5-O-tert-butyldiphenylsilyl-α-D-ribofuranoside

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; In diethyl ether; for 0.5h;
DOI:10.1016/S0040-4039(97)01811-X

Reference yield:

: 197644-79-4
(2'S,3'S)-ethyl 3,4-di-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-β-D-glucopyranoside

: 197644-81-8
(2S,3S)-3-O-[2',6'-di-O-benzyl-3',4'-di-O-(2,3-dimethoxybutane-2,3-diyl)-α-D-glucopyranosyl]-1,2-O-isopropylidene-5-O-tert-butyldiphenylsilyl-α-D-ribofuranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydride / dimethylformamide / 0.25 h / 0 °C

1.2: 98 percent / dimethylformamide

2.1: 83 percent / molecular sieves 4A; N-iodosuccinimide; trifluoromethanesulfonic acid / diethyl ether / 0.75 h / 20 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; sodium hydride; In diethyl ether; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: benzylation / 2.1: glycosylation;
DOI:10.1021/jm000957c

Reference yield:

: 32934-24-0,41670-79-5,52645-73-5,55722-49-1,79389-52-9,99031-86-4,125354-48-5,126187-25-5
ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside

: 197644-81-8
(2S,3S)-3-O-[2',6'-di-O-benzyl-3',4'-di-O-(2,3-dimethoxybutane-2,3-diyl)-α-D-glucopyranosyl]-1,2-O-isopropylidene-5-O-tert-butyldiphenylsilyl-α-D-ribofuranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaOMe; methanol

2.1: camphorosulfonic acid / methanol / 3 h / Heating

3.1: sodium hydride / dimethylformamide / 0.25 h / 0 °C

3.2: 98 percent / dimethylformamide

4.1: 83 percent / molecular sieves 4A; N-iodosuccinimide; trifluoromethanesulfonic acid / diethyl ether / 0.75 h / 20 °C

With methanol; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; camphor-10-sulfonic acid; sodium methylate; sodium hydride; In methanol; diethyl ether; N,N-dimethyl-formamide; 1.1: Deacetylation / 2.1: Condensation / 3.1: Metallation / 3.2: benzylation / 4.1: glycosylation;
DOI:10.1021/jm000957c