5-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hex-5-en-1-ol

Base Information

• Chemical Name: 5-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hex-5-en-1-ol
• CAS No.: 118715-33-6
• Molecular Formula: C₄₀H₄₆O₇
• Molecular Weight: 638.801

Synonyms:5-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hex-5-en-1-ol

Chemical Property of 5-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hex-5-en-1-ol

Chemical Property:

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Technology Process of 5-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hex-5-en-1-ol

There total 4 articles about 5-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hex-5-en-1-ol 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:

tert-Butyl-diphenyl-[5-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hex-5-enyloxy]-silane (118715-30-3) → 5-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hex-5-en-1-ol (118715-33-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1021/ja00186a037

Reference yield:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) → 5-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hex-5-en-1-ol (118715-33-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) n-BuLi / 1.) THF, -78 deg C

2: 86 percent / pyridine; tetrahydrofuran; toluene / -40 - 0 °C

3: Bu₄NF / tetrahydrofuran

With n-butyllithium; tetrabutyl ammonium fluoride; In tetrahydrofuran; pyridine; toluene;

DOI:10.1021/ja00186a037

Reference yield:

5-<(tert-Butyldiphenylsilyl)oxy>pentanoyl chloride (118715-28-9) → 5-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hex-5-en-1-ol (118715-33-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) n-BuLi / 1.) THF, -78 deg C

2: 86 percent / pyridine; tetrahydrofuran; toluene / -40 - 0 °C

3: Bu₄NF / tetrahydrofuran

With n-butyllithium; tetrabutyl ammonium fluoride; In tetrahydrofuran; pyridine; toluene;

DOI:10.1021/ja00186a037

upstream raw materials:

tert-Butyl-diphenyl-[5-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hex-5-enyloxy]-silane

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

5-<(tert-Butyldiphenylsilyl)oxy>pentanoyl chloride

5-(tert-Butyl-diphenyl-silanyloxy)-pentanoic acid (2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

Downstream raw materials:

(2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2-iodomethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran

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