(+/-)-4,5,7,8-tetra-O-acetyl-2-O-benzyl-3-deoxy-D-manno-2-octulopyranosonate

Base Information

• Chemical Name: (+/-)-4,5,7,8-tetra-O-acetyl-2-O-benzyl-3-deoxy-D-manno-2-octulopyranosonate
• CAS No.: 92622-41-8
• Molecular Formula: C₂₃H₂₈O₁₂
• Molecular Weight: 496.468
• Mol file: 92622-41-8.mol

Synonyms:(+/-)-4,5,7,8-tetra-O-acetyl-2-O-benzyl-3-deoxy-D-manno-2-octulopyranosonate

Chemical Property of (+/-)-4,5,7,8-tetra-O-acetyl-2-O-benzyl-3-deoxy-D-manno-2-octulopyranosonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-4,5,7,8-tetra-O-acetyl-2-O-benzyl-3-deoxy-D-manno-2-octulopyranosonate

There total 3 articles about (+/-)-4,5,7,8-tetra-O-acetyl-2-O-benzyl-3-deoxy-D-manno-2-octulopyranosonate 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: 86.0%

(2R*,4R*,5S*,6R*,1R*)-4,5-bis(acetyloxy)-2-(benzyloxy)-2-(α-furyl)-6-(1,2-diacetoxyethyl)tetrahydropyran (92622-40-7) → (+/-)-4,5,7,8-tetra-O-acetyl-2-O-benzyl-3-deoxy-D-manno-2-octulopyranosonate (92622-41-8)

Guidance literature:

With ruthenium(IV) oxide; sodium periodate; In tetrachloromethane; water; acetonitrile; for 2h;

DOI:10.1021/ja00291a030

Reference yield:

(2R*,4R*,5S*,6R*)-4,5-bis(acetyloxy)-2-(benzyloxy)-2-(α-furyl)-6-vinyltetrahydropyran (92622-38-3) → (+/-)-4,5,7,8-tetra-O-acetyl-2-O-benzyl-3-deoxy-D-manno-2-octulopyranosonate (92622-41-8)

Guidance literature:

Multi-step reaction with 3 steps

1: osmium tetraoxide / tetrahydrofuran; H₂O; CH₂Cl₂ / 4.5 h

2: pyridine / 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h

3: 86 percent / ruthenium dioxide (RuO₂), sodium periodate (NaIO₄) / H₂O; CCl₄; acetonitrile / 2 h

With pyridine; ruthenium(IV) oxide; sodium periodate; osmium(VIII) oxide; dmap; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1021/ja00291a030

Reference yield:

Acetic acid (2S,4S,5S,6S)-5-acetoxy-2-benzyloxy-6-((S)-1,2-dihydroxy-ethyl)-2-furan-2-yl-tetrahydro-pyran-4-yl ester (92622-39-4) → (+/-)-4,5,7,8-tetra-O-acetyl-2-O-benzyl-3-deoxy-D-manno-2-octulopyranosonate (92622-41-8)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h

2: 86 percent / ruthenium dioxide (RuO₂), sodium periodate (NaIO₄) / H₂O; CCl₄; acetonitrile / 2 h

With pyridine; ruthenium(IV) oxide; sodium periodate; dmap; In tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1021/ja00291a030

upstream raw materials:

(2R*,4R*,5S*,6R*,1R*)-4,5-bis(acetyloxy)-2-(benzyloxy)-2-(α-furyl)-6-(1,2-diacetoxyethyl)tetrahydropyran

(2R*,4R*,5S*,6R*)-4,5-bis(acetyloxy)-2-(benzyloxy)-2-(α-furyl)-6-vinyltetrahydropyran

Acetic acid (2S,4S,5S,6S)-5-acetoxy-2-benzyloxy-6-((S)-1,2-dihydroxy-ethyl)-2-furan-2-yl-tetrahydro-pyran-4-yl ester

Downstream raw materials:

(+/-)-methyl 4,5,7,8-tetra-O-acetyl-2-O-benzyl-3-deoxy-D-manno-2-octulopyranosonate