Acetic acid (2S,3R,4S,5S,6S)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5S,6S)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 113466-57-2
• Molecular Formula: C₃₂H₃₆O₆
• Molecular Weight: 516.634
• Mol file: 113466-57-2.mol

Synonyms:Acetic acid (2S,3R,4S,5S,6S)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Acetic acid (2S,3R,4S,5S,6S)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3R,4S,5S,6S)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester

There total 2 articles about Acetic acid (2S,3R,4S,5S,6S)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester 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: 83.0%

Acetic acid (2S,3R,4R,5R,6S)-6-acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl ester (4356-77-8,35094-65-6,59433-13-5,61277-56-3,65556-30-1,78185-13-4,78185-15-6,109958-31-8,109958-33-0,113532-02-8) + allyl-trimethyl-silane (762-72-1) → Acetic acid (2S,3R,4S,5S,6S)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester (113466-57-2)

Guidance literature:

With boron trifluoride diethyl etherate; at 0 ℃;

DOI:10.1016/S0040-4039(00)96327-5

Reference yield:

benzyl bromide (100-39-0) → Acetic acid (2S,3R,4S,5S,6S)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester (113466-57-2)

Guidance literature:

Multi-step reaction with 2 steps

2: 83 percent / BF₃*Et₂O / 0 °C

With boron trifluoride diethyl etherate;

DOI:10.1016/S0040-4039(00)96327-5

Reference yield:

Acetic acid (2S,3R,4S,5S,6S)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester (113466-57-2) → ((2S,3R,4S,5S,6S)-6-Allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-methanol (82614-11-7,133697-15-1)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃;

DOI:10.1016/S0040-4039(00)96327-5

upstream raw materials:

Acetic acid (2S,3R,4R,5R,6S)-6-acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl ester

allyl-trimethyl-silane

benzyl bromide

Downstream raw materials:

((2S,3R,4S,5S,6S)-6-Allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-methanol

[(3aR,4S,5aS,8R,9aS,9bS)-4-Hydroxymethyl-2-(4-methoxy-phenyl)-octahydro-[1,3]dioxolo[4,5-d]pyrano[3,2-b]pyran-8-yl]-acetic acid methyl ester

[(3aR,4S,5aS,8R,9aS,9bS)-4-[(S)-1-Hydroxy-3-(2-pentyl-[1,3]dioxan-2-yl)-prop-2-ynyl]-2-(4-methoxy-phenyl)-octahydro-[1,3]dioxolo[4,5-d]pyrano[3,2-b]pyran-8-yl]-acetic acid methyl ester

[(3aR,4S,5aS,8R,9aS,9bS)-4-[(R)-1-Hydroxy-3-(2-pentyl-[1,3]dioxan-2-yl)-prop-2-ynyl]-2-(4-methoxy-phenyl)-octahydro-[1,3]dioxolo[4,5-d]pyrano[3,2-b]pyran-8-yl]-acetic acid methyl ester