3-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol

Base Information

• Chemical Name: 3-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol
• CAS No.: 240137-98-8
• Molecular Formula: C₃₇H₃₈O₆
• Molecular Weight: 578.705
• Mol file: 240137-98-8.mol

Synonyms:3-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol

Chemical Property of 3-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol

There total 2 articles about 3-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-prop-2-yn-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: 65.0%

(3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-tetrahydro-pyran-2-ol → 3-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol (240137-98-8)

Guidance literature:

(3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-tetrahydro-pyran-2-ol; With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 - 20 ℃; for 2h;

With water; In dichloromethane;

DOI:10.1055/s-1999-3165

Reference yield:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) → 3-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol (240137-98-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrahydrofuran / 1.5 h / -78 - 0 °C

2.1: Et₃SiH; BF₃*Et₂O / CH₂Cl₂ / 2 h / -78 - 20 °C

2.2: 65 percent / H₂O / CH₂Cl₂

With triethylsilane; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane; 1.1: Addition / 2.1: Reduction / 2.2: Hydrolysis;

DOI:10.1055/s-1999-3165

Reference yield: 86.0%

3-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol (240137-98-8) → 1-(2,3,4,6-O-tetrabenzyl-β-D-glucopyranosyl)-1-propen-3-ol (136172-67-3)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether; at 0 ℃; for 1h;

DOI:10.1055/s-1999-3165

upstream raw materials:

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

Downstream raw materials:

1-(2,3,4,6-O-tetrabenzyl-β-D-glucopyranosyl)-1-propen-3-ol

(E)-3-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propenal

2-[(E)-3-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-prop-2-en-(E)-ylidene]-succinic acid 1-ethyl ester