1-O-Acetyl-3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranose

Base Information

• Chemical Name: 1-O-Acetyl-3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranose
• CAS No.: 132674-50-1
• Molecular Formula: C₂₉H₃₂O₆
• Molecular Weight: 476.569
• Mol file: 132674-50-1.mol

Synonyms:1-O-Acetyl-3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranose

Chemical Property of 1-O-Acetyl-3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-Acetyl-3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranose

There total 5 articles about 1-O-Acetyl-3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranose 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: 93.0%

acetic acid (64-19-7,77671-22-8) + 2-S-(3',4',6'-tri-O-benzyl-2'-deoxy-α-D-arabino-hexopyranosyl)-5,5-dimethyl-1,3,2-dioxa-2-thiolo-2-thioxophosphorinane (133857-94-0) → 1-O-Acetyl-3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranose (132674-50-1)

Guidance literature:

With molecular sieve; silver carbonate; In dichloromethane; for 48h; Ambient temperature;

DOI:10.1055/s-1994-25554

Reference yield: 69.0%

(4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-one (79999-46-5,72605-77-7) + acetic anhydride (108-24-7) → 1-O-Acetyl-3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranose (132674-50-1)

Guidance literature:

(4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-one; With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 4h; Inert atmosphere;

acetic anhydride; With pyridine; dmap; In dichloromethane; toluene; Inert atmosphere;

DOI:10.1021/jo8017846

Reference yield:

3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose (160549-11-1) + acetyl chloride (75-36-5) → 1-O-Acetyl-3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranose (132674-50-1) + 1-O-Acetyl-3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranose (132674-49-8)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 20 ℃; Overall yield = 65 %;

upstream raw materials:

3,4,6-tri-O-benzyl-D-glucal

acetic acid

2-S-(3',4',6'-tri-O-benzyl-2'-deoxy-α-D-arabino-hexopyranosyl)-5,5-dimethyl-1,3,2-dioxa-2-thiolo-2-thioxophosphorinane

acetic anhydride

Downstream raw materials:

3,4,6-tri-O-benzyl-1,2-dideoxy-1β-(prop-2-enyl)-D-arabino-hexopyranose

(2R,3S,4R,6R)-6-allyl-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)tetrahydro-2H-pyran