tert-butyldimethyl((2R,3S,4S)-1,3,4-tris(benzyloxy)hex-5-en-2-yloxy)silane

Base Information

• Chemical Name: tert-butyldimethyl((2R,3S,4S)-1,3,4-tris(benzyloxy)hex-5-en-2-yloxy)silane
• CAS No.: 1338246-45-9
• Molecular Formula: C₃₃H₄₄O₄Si
• Molecular Weight: 532.795

Synonyms:tert-butyldimethyl((2R,3S,4S)-1,3,4-tris(benzyloxy)hex-5-en-2-yloxy)silane

Chemical Property of tert-butyldimethyl((2R,3S,4S)-1,3,4-tris(benzyloxy)hex-5-en-2-yloxy)silane

Chemical Property:

Purity/Quality:

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Technology Process of tert-butyldimethyl((2R,3S,4S)-1,3,4-tris(benzyloxy)hex-5-en-2-yloxy)silane

There total 2 articles about tert-butyldimethyl((2R,3S,4S)-1,3,4-tris(benzyloxy)hex-5-en-2-yloxy)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: 98.0%

t-butyldimethylsiyl triflate (69739-34-0) + (2R,3R,4S)-1,3,4-tris(benzyloxy)hex-5-en-2-ol (93125-78-1) → tert-butyldimethyl((2R,3S,4S)-1,3,4-tris(benzyloxy)hex-5-en-2-yloxy)silane (1338246-45-9)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; Inert atmosphere;

DOI:10.1021/ol202121k

Reference yield:

2,3,5-tri-O-benzyl-D-ribofuranose (16838-89-4) → tert-butyldimethyl((2R,3S,4S)-1,3,4-tris(benzyloxy)hex-5-en-2-yloxy)silane (1338246-45-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0 - 20 °C / Inert atmosphere

1.2: 0 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / 0 °C / Inert atmosphere

With 2,6-dimethylpyridine; n-butyllithium; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/ol202121k

Reference yield: 70.0%

tert-butyldimethyl((2R,3S,4S)-1,3,4-tris(benzyloxy)hex-5-en-2-yloxy)silane (1338246-45-9) → tert-butyldimethyl((2R,3S,4S)-1,3,4-tris(benzyloxy)-4-(oxiran-2-yl)butan-2-yloxy)silane (1337989-75-9)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol202121k

upstream raw materials:

2,3,5-tri-O-benzyl-D-ribofuranose

t-butyldimethylsiyl triflate

(2R,3R,4S)-1,3,4-tris(benzyloxy)hex-5-en-2-ol

Downstream raw materials:

tert-butyldimethyl((2R,3S,4S)-1,3,4-tris(benzyloxy)-4-(oxiran-2-yl)butan-2-yloxy)silane

5-((tetrahydro-2H-pyran-2-yloxy)methyl)-1-((3S,4S,5R)-3,4,6-tris(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2-hydroxyhexyl)-1H-pyrrole-2-carbaldehyde

5-((tert-butyldimethylsilyloxy)methyl)-1-((3S,4S,5R)-3,4,6-tris(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2-hydroxyhexyl)-1H-pyrrole-2-carbaldehyde

5-((tetrahydro-2H-pyran-2-yloxy)methyl)-1-((3R,4S,5R)-3,4,6-tris(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2-oxohexyl)-1H-pyrrole-2-carbaldehyde

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