((2S,3R,4R,5S,6S)-3-Azido-4,5-bis-benzyloxy-6-benzylsulfanylmethyl-tetrahydro-pyran-2-yloxy)-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: ((2S,3R,4R,5S,6S)-3-Azido-4,5-bis-benzyloxy-6-benzylsulfanylmethyl-tetrahydro-pyran-2-yloxy)-tert-butyl-dimethyl-silane
• CAS No.: 852371-70-1
• Molecular Formula: C₃₃H₄₃N₃O₄SSi
• Molecular Weight: 605.874

Synonyms:((2S,3R,4R,5S,6S)-3-Azido-4,5-bis-benzyloxy-6-benzylsulfanylmethyl-tetrahydro-pyran-2-yloxy)-tert-butyl-dimethyl-silane

Chemical Property of ((2S,3R,4R,5S,6S)-3-Azido-4,5-bis-benzyloxy-6-benzylsulfanylmethyl-tetrahydro-pyran-2-yloxy)-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

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Technology Process of ((2S,3R,4R,5S,6S)-3-Azido-4,5-bis-benzyloxy-6-benzylsulfanylmethyl-tetrahydro-pyran-2-yloxy)-tert-butyl-dimethyl-silane

There total 2 articles about ((2S,3R,4R,5S,6S)-3-Azido-4,5-bis-benzyloxy-6-benzylsulfanylmethyl-tetrahydro-pyran-2-yloxy)-tert-butyl-dimethyl-silane 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: 77.0%

lithium phenylmethanethiolate (52791-97-6) + Toluene-4-sulfonic acid (2R,3S,4R,5R,6S)-5-azido-3,4-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester (852371-69-8) → ((2S,3R,4R,5S,6S)-3-Azido-4,5-bis-benzyloxy-6-benzylsulfanylmethyl-tetrahydro-pyran-2-yloxy)-tert-butyl-dimethyl-silane (852371-70-1)

Guidance literature:

In tetrahydrofuran; at 0 - 25 ℃;

DOI:10.1016/j.bmcl.2005.02.061

Reference yield:

2-azido-2-deoxy-3,4-O-dibenzyl-1-O-tert-butyldimethylsilyl-β-D-glucopyranoside (129891-66-3) → ((2S,3R,4R,5S,6S)-3-Azido-4,5-bis-benzyloxy-6-benzylsulfanylmethyl-tetrahydro-pyran-2-yloxy)-tert-butyl-dimethyl-silane (852371-70-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / pyridine

2: 77 percent / tetrahydrofuran / 0 - 25 °C

With pyridine; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2005.02.061

Reference yield: 86.0%

((2S,3R,4R,5S,6S)-3-Azido-4,5-bis-benzyloxy-6-benzylsulfanylmethyl-tetrahydro-pyran-2-yloxy)-tert-butyl-dimethyl-silane (852371-70-1) → (3R,4R,5S,6S)-3-Azido-4,5-bis-benzyloxy-6-benzylsulfanylmethyl-tetrahydro-pyran-2-ol

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2005.02.061

upstream raw materials:

lithium phenylmethanethiolate

Toluene-4-sulfonic acid (2R,3S,4R,5R,6S)-5-azido-3,4-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester

2-azido-2-deoxy-3,4-O-dibenzyl-1-O-tert-butyldimethylsilyl-β-D-glucopyranoside

Downstream raw materials:

(1S,2R,3S,4S,5R,6S)-3-((2S,3R,4R,5S,6S)-3-Azido-4,5-bis-benzyloxy-6-benzylsulfanylmethyl-tetrahydro-pyran-2-yloxy)-4,5,6-tris-benzyloxy-cyclohexane-1,2-diol

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