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

Base Information

• Chemical Name: (2R*,4R*,5S*,6R*,1R*)-4,5-bis(acetyloxy)-2-(benzyloxy)-2-(α-furyl)-6-(1,2-diacetoxyethyl)tetrahydropyran
• CAS No.: 92622-40-7
• Molecular Formula: C₂₆H₃₀O₁₁
• Molecular Weight: 518.518
• Mol file: 92622-40-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (2R*,4R*,5S*,6R*,1R*)-4,5-bis(acetyloxy)-2-(benzyloxy)-2-(α-furyl)-6-(1,2-diacetoxyethyl)tetrahydropyran 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:

(2R*,4R*,5S*,6R*)-4,5-bis(acetyloxy)-2-(benzyloxy)-2-(α-furyl)-6-vinyltetrahydropyran (92622-38-3) → (2R*,4R*,5S*,6R*,1R*)-4,5-bis(acetyloxy)-2-(benzyloxy)-2-(α-furyl)-6-(1,2-diacetoxyethyl)tetrahydropyran (92622-40-7)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With pyridine; osmium(VIII) oxide; dmap; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/ja00291a030

Reference yield:

acetic anhydride (108-24-7) + 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) → (2R*,4R*,5S*,6R*,1R*)-4,5-bis(acetyloxy)-2-(benzyloxy)-2-(α-furyl)-6-(1,2-diacetoxyethyl)tetrahydropyran (92622-40-7)

Guidance literature:

With pyridine; dmap; In dichloromethane; for 2h; Yield given;

DOI:10.1021/ja00291a030

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

upstream raw materials:

acetic anhydride

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

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

Downstream raw materials:

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

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