(2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(but-3-enyl)tetrahydro-2H-pyran-2-ol

Base Information

• Chemical Name: (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(but-3-enyl)tetrahydro-2H-pyran-2-ol
• CAS No.: 190505-14-7
• Molecular Formula: C₃₈H₄₂O₆
• Molecular Weight: 594.748
• Mol file: 190505-14-7.mol

Synonyms:(2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(but-3-enyl)tetrahydro-2H-pyran-2-ol

Chemical Property of (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(but-3-enyl)tetrahydro-2H-pyran-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(but-3-enyl)tetrahydro-2H-pyran-2-ol

There total 2 articles about (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(but-3-enyl)tetrahydro-2H-pyran-2-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: 88.0%

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) + 4-but-1-enylmagnesium bromide (7103-09-5) → (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(but-3-enyl)tetrahydro-2H-pyran-2-ol (190505-14-7)

Guidance literature:

In diethyl ether; at -78 ℃; for 2h;

DOI:10.1016/S0040-4020(97)00273-1

Reference yield:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) + vinyl magnesium bromide (1826-67-1) → (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(but-3-enyl)tetrahydro-2H-pyran-2-ol (190505-14-7)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 2.5h;

DOI:10.1021/jo034795e

Reference yield: 97.0%

(2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(but-3-enyl)tetrahydro-2H-pyran-2-ol (190505-14-7) → 1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-3-butene (190505-15-8)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In acetonitrile; at -18 ℃; for 0.166667h;

DOI:10.1016/S0040-4020(97)00273-1

upstream raw materials:

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

4-but-1-enylmagnesium bromide

vinyl magnesium bromide

Downstream raw materials:

1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-3-butene

1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-3,4-butandiol

Hexadecanoic acid 1-hexadecanoyloxymethyl-3-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl ester

(2S,3R,4S,5R,6R)-2-azido-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(but-3-enyl)tetrahydro-2H-pyran