phenyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzyl-3,4-di-O-TIPS-α-L-rhamnopyranosyl)-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:phenyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzyl-3,4-di-O-TIPS-α-L-rhamnopyranosyl)-1-thio-β-D-glucopyranoside
CAS No.:1382229-40-4
Molecular Formula:C₆₄H₉₀O₉SSi₂
Molecular Weight:1091.65
Hs Code.:

Synonyms:phenyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzyl-3,4-di-O-TIPS-α-L-rhamnopyranosyl)-1-thio-β-D-glucopyranoside

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Chemical Property of phenyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzyl-3,4-di-O-TIPS-α-L-rhamnopyranosyl)-1-thio-β-D-glucopyranoside

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Technology Process of phenyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzyl-3,4-di-O-TIPS-α-L-rhamnopyranosyl)-1-thio-β-D-glucopyranoside

There total 6 articles about phenyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzyl-3,4-di-O-TIPS-α-L-rhamnopyranosyl)-1-thio-β-D-glucopyranoside 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: 66.0%

: 1382228-82-1
phenyl 2-O-benzyl-3,4-di-O-TIPS-1-thio-α-L-rhamnopyranoside

: 97974-20-4
(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol

: 1382229-40-4
phenyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzyl-3,4-di-O-TIPS-α-L-rhamnopyranosyl)-1-thio-β-D-glucopyranoside

Guidance literature:: phenyl 2-O-benzyl-3,4-di-O-TIPS-1-thio-α-L-rhamnopyranoside; (2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol; In dichloromethane; for 1h; Molecular sieve;

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -78 ℃; optical yield given as %de; diastereoselective reaction;
DOI:10.1021/jo300591k

Reference yield:

: C₁₈H₂₆O₆S

: 1382229-40-4
phenyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzyl-3,4-di-O-TIPS-α-L-rhamnopyranosyl)-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide

2.1: water; trifluoroacetic acid / dichloromethane

3.1: 2,6-dimethylpyridine / 80 °C

4.1: dichloromethane / 1 h / Molecular sieve

4.2: -78 °C

With 2,6-dimethylpyridine; water; sodium hydride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo300591k

Reference yield:

: 849938-16-5
phenyl 2-O-benzyl-1-thio-α-L-rhamnopyranoside

: 1382229-40-4
phenyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzyl-3,4-di-O-TIPS-α-L-rhamnopyranosyl)-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: 2,6-dimethylpyridine / 80 °C

2.1: dichloromethane / 1 h / Molecular sieve

2.2: -78 °C

With 2,6-dimethylpyridine; In dichloromethane;
DOI:10.1021/jo300591k