Acetic acid (E)-2-methyl-3-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propenyl ester

Base Information

• Chemical Name: Acetic acid (E)-2-methyl-3-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propenyl ester
• CAS No.: 120520-64-1
• Molecular Formula: C₄₀H₄₄O₇
• Molecular Weight: 636.785
• Mol file: 120520-64-1.mol

Synonyms:

Chemical Property of Acetic acid (E)-2-methyl-3-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (E)-2-methyl-3-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propenyl ester

There total 2 articles about Acetic acid (E)-2-methyl-3-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propenyl 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: 70.0%

1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside (56822-49-2) + <1-(acetyloxy)-2-methyl-2-propenyl>trimethylsilane (120417-01-8) → Acetic acid (E)-2-methyl-3-((3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propenyl ester (120417-04-1,120520-56-1,120520-57-2,120520-58-3,120520-63-0,120520-64-1,120520-65-2,120520-66-3)

Guidance literature:

With boron trifluoride diethyl etherate; In 1,2-dichloro-ethane; at 10 ℃; for 24h;

DOI:10.1021/jo00270a005

Reference yield: 65.0%

<1-(acetyloxy)-2-methyl-2-propenyl>trimethylsilane (120417-01-8) + 2,3,4,6-tetra-O-benzyl-1-O-acetyl-α-D-mannopyranose (3866-62-4,3964-13-4,56822-48-1,56822-49-2,78136-22-8,80300-30-7,80300-97-6,83462-69-5,94943-10-9,83462-68-4) → Acetic acid (E)-2-methyl-3-((3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propenyl ester (120417-04-1,120520-56-1,120520-57-2,120520-58-3,120520-63-0,120520-64-1,120520-65-2,120520-66-3)

Guidance literature:

With boron trifluoride diethyl etherate; In 1,2-dichloro-ethane; at 10 ℃; for 30h;

DOI:10.1021/jo00270a005

Reference yield:

Acetic acid (E)-2-methyl-3-((2S,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propenyl ester (120417-04-1,120520-56-1,120520-57-2,120520-58-3,120520-63-0,120520-64-1,120520-65-2,120520-66-3) → 1-((2S,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propan-2-one (120520-83-4)

Guidance literature:

With lead(IV) acetate; trimethylamine-N-oxide; osmium(VIII) oxide; Yield given. Multistep reaction; 2) MeOH;

DOI:10.1016/S0040-4039(00)95213-4

upstream raw materials:

<1-(acetyloxy)-2-methyl-2-propenyl>trimethylsilane

2,3,4,6-tetra-O-benzyl-1-O-acetyl-α-D-mannopyranose

1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside

Downstream raw materials:

1-((2S,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propan-2-one

1-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propan-2-one

4,8-anhydro-5,6,7,9-tetra-O-benzyl-1,3-dideoxy-D-glycero-D-gulo-non-2-ulose

1-(2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl)-2-propanon