1-C-(6'-O-acetyl-3',4'-di-O-benzyl-2'-O-tosyl-α-D-mannopyranosyl)-acetone

Base Information

• Chemical Name: 1-C-(6'-O-acetyl-3',4'-di-O-benzyl-2'-O-tosyl-α-D-mannopyranosyl)-acetone
• CAS No.: 1073478-35-9
• Molecular Formula: C₃₂H₃₆O₉S
• Molecular Weight: 596.698
• Mol file: 1073478-35-9.mol

Synonyms:1-C-(6'-O-acetyl-3',4'-di-O-benzyl-2'-O-tosyl-α-D-mannopyranosyl)-acetone

Chemical Property of 1-C-(6'-O-acetyl-3',4'-di-O-benzyl-2'-O-tosyl-α-D-mannopyranosyl)-acetone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-C-(6'-O-acetyl-3',4'-di-O-benzyl-2'-O-tosyl-α-D-mannopyranosyl)-acetone

There total 4 articles about 1-C-(6'-O-acetyl-3',4'-di-O-benzyl-2'-O-tosyl-α-D-mannopyranosyl)-acetone 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%

3-C-(3',4',6'-tri-O-benzyl-2'-O-tosyl-α-D-mannopyranosyl)-acetone (857419-66-0) + acetic anhydride (108-24-7) → 1-C-(6'-O-acetyl-3',4'-di-O-benzyl-2'-O-tosyl-α-D-mannopyranosyl)-acetone (1073478-35-9)

Guidance literature:

With zinc(II) chloride; In acetic acid; at 0 - 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/jo1016579

Reference yield:

1-(3',4',6'-tri-O-benzyl-α-D-mannopyranosyl)prop-2-ene (767340-70-5) → 1-C-(6'-O-acetyl-3',4'-di-O-benzyl-2'-O-tosyl-α-D-mannopyranosyl)-acetone (1073478-35-9)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / dichloromethane / 20 °C

2: Jones reagent; mercury(II) diacetate / water; acetone / 6 h / 0 °C

3: zinc(II) chloride / acetic acid / 16 h / 0 - 20 °C / Inert atmosphere

With pyridine; Jones reagent; mercury(II) diacetate; zinc(II) chloride; In dichloromethane; water; acetic acid; acetone;

DOI:10.1021/jo1016579

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → 1-C-(6'-O-acetyl-3',4'-di-O-benzyl-2'-O-tosyl-α-D-mannopyranosyl)-acetone (1073478-35-9)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / dichloromethane / 20 °C

2: Jones reagent; mercury(II) diacetate / water; acetone / 6 h / 0 °C

3: zinc(II) chloride / acetic acid / 16 h / 0 - 20 °C / Inert atmosphere

With pyridine; Jones reagent; mercury(II) diacetate; zinc(II) chloride; In dichloromethane; water; acetic acid; acetone;

DOI:10.1021/jo1016579

upstream raw materials:

1-(3',4',6'-tri-O-benzyl-α-D-mannopyranosyl)prop-2-ene

3-C-(3',4',6'-tri-O-benzyl-2'-O-tosyl-α-D-mannopyranosyl)-propene

3-C-(3',4',6'-tri-O-benzyl-2'-O-tosyl-α-D-mannopyranosyl)-acetone

acetic anhydride

Downstream raw materials:

1'-C-acetyl-6-O-acetyl-3,4-di-O-benzyl-1,2-cyclopropane-1,2-deoxyl-α-D-glucopyranose

1,2;3,4-di-O-isopropylidene-6-O-(6'-O-acetyl-3',4'-di-O-benzyl-2'-C-acetylmethyl-2'-deoxy-β-D-glucopyranosyl)-α-D-galactopyranoside

C₂₄H₂₈O₇S

(2S,3aR,4R,5S,6R,7aR)-2-allyl-4,5-bis(benzyloxy)-6-[(methanesulfonyloxy)methyl]2-methylhexahydro-furo[2,3-b]pyran