(2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-2-((E)-4-benzyloxy-but-1-enyl)-6-benzyloxymethyl-tetrahydro-pyran

Base Information

Chemical Name:(2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-2-((E)-4-benzyloxy-but-1-enyl)-6-benzyloxymethyl-tetrahydro-pyran
CAS No.:88970-20-1
Molecular Formula:C₄₅H₄₈O₆
Molecular Weight:684.873
Hs Code.:

Synonyms:(2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-2-((E)-4-benzyloxy-but-1-enyl)-6-benzyloxymethyl-tetrahydro-pyran

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Chemical Property of (2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-2-((E)-4-benzyloxy-but-1-enyl)-6-benzyloxymethyl-tetrahydro-pyran

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Technology Process of (2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-2-((E)-4-benzyloxy-but-1-enyl)-6-benzyloxymethyl-tetrahydro-pyran

There total 5 articles about (2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-2-((E)-4-benzyloxy-but-1-enyl)-6-benzyloxymethyl-tetrahydro-pyran 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: 57.0%

: 88970-19-8
(2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-2-(4-benzyloxy-but-1-ynyl)-6-benzyloxymethyl-tetrahydro-pyran

: 88970-20-1
(2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-2-((E)-4-benzyloxy-but-1-enyl)-6-benzyloxymethyl-tetrahydro-pyran

Guidance literature:: With lithium aluminium tetrahydride; In 1,2-dimethoxyethane; at 90 ℃; for 12h;
DOI:10.1016/S0040-4039(00)94019-X

Reference yield:

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 88970-20-1
(2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-2-((E)-4-benzyloxy-but-1-enyl)-6-benzyloxymethyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 3 steps

1: n-BuLi / tetrahydrofuran / 1.5 h / -78 - -40 °C

2: 72 percent / Et₃SiH, BF₃*Et₂O / acetonitrile; CH₂Cl₂ / 1 h / -40 °C

3: 57 percent / LiAlH₄ / 1,2-dimethoxy-ethane / 12 h / 90 °C

With triethylsilane; lithium aluminium tetrahydride; n-butyllithium; boron trifluoride diethyl etherate; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; acetonitrile;
DOI:10.1016/S0040-4039(00)94019-X

Reference yield:

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

: 88970-20-1
(2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-2-((E)-4-benzyloxy-but-1-enyl)-6-benzyloxymethyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 4 steps

1: 94 percent

2: n-BuLi / tetrahydrofuran / 1.5 h / -78 - -40 °C

3: 72 percent / Et₃SiH, BF₃*Et₂O / acetonitrile; CH₂Cl₂ / 1 h / -40 °C

4: 57 percent / LiAlH₄ / 1,2-dimethoxy-ethane / 12 h / 90 °C

With triethylsilane; lithium aluminium tetrahydride; n-butyllithium; boron trifluoride diethyl etherate; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; acetonitrile;
DOI:10.1016/S0040-4039(00)94019-X