9-O-acetyl-4,8-anhydro-5,6,7-tri-O-benzyl-1,2,3-trideoxy-D-glycero-D-galacto-non-1-enitol

Base Information

• Chemical Name: 9-O-acetyl-4,8-anhydro-5,6,7-tri-O-benzyl-1,2,3-trideoxy-D-glycero-D-galacto-non-1-enitol
• CAS No.: 194410-25-8
• Molecular Formula: C₃₂H₃₆O₆
• Molecular Weight: 516.634
• Mol file: 194410-25-8.mol

Synonyms:9-O-acetyl-4,8-anhydro-5,6,7-tri-O-benzyl-1,2,3-trideoxy-D-glycero-D-galacto-non-1-enitol

Chemical Property of 9-O-acetyl-4,8-anhydro-5,6,7-tri-O-benzyl-1,2,3-trideoxy-D-glycero-D-galacto-non-1-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-O-acetyl-4,8-anhydro-5,6,7-tri-O-benzyl-1,2,3-trideoxy-D-glycero-D-galacto-non-1-enitol

There total 5 articles about 9-O-acetyl-4,8-anhydro-5,6,7-tri-O-benzyl-1,2,3-trideoxy-D-glycero-D-galacto-non-1-enitol 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: 95.0%

1,6-di-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranoside (65556-30-1) + allyl-trimethyl-silane (762-72-1) → 9-O-acetyl-4,8-anhydro-5,6,7-tri-O-benzyl-1,2,3-trideoxy-D-glycero-D-galacto-non-1-enitol (194410-25-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 0.25h; Inert atmosphere; Sonication;

DOI:10.1016/j.tetlet.2010.10.113

Reference yield: 87.0%

acetic anhydride (108-24-7) + (2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran (3879-79-6,17791-37-6,19488-61-0,53008-63-2,69237-94-1,69237-95-2,71526-33-5,83462-67-3,84799-77-9,103421-29-0,103421-30-3,139241-42-2,61330-62-9) + allyl-trimethyl-silane (762-72-1) → 9-O-acetyl-4,8-anhydro-5,6,7-tri-O-benzyl-1,2,3-trideoxy-D-glycero-D-galacto-non-1-enitol (194410-25-8)

Guidance literature:

(2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran; allyl-trimethyl-silane; With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 4 ℃; for 24h;

acetic anhydride; at 0 ℃; for 2h;

DOI:10.1016/S0008-6215(02)00206-9

Reference yield: 70.0%

acetic anhydride (108-24-7) + 3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)propene (82659-59-4) → 9-O-acetyl-4,8-anhydro-5,6,7-tri-O-benzyl-1,2,3-trideoxy-D-glycero-D-galacto-non-1-enitol (194410-25-8)

Guidance literature:

With sulfuric acid; at 0 - 20 ℃; for 16h;

DOI:10.1021/jo034446k

upstream raw materials:

acetic anhydride

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

allyl-trimethyl-silane

3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)propene

Downstream raw materials:

8-O-acetyl-3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-glycero-D-galacto-octose

3-(6-O-hexadecanyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)propene

((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hexadecyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid

3-[2-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hexadecyloxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-benzoic acid