(1'R,3'S)-2',2'-dichloro-3'-hydroxycyclobutyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside

Base Information

• Chemical Name: (1'R,3'S)-2',2'-dichloro-3'-hydroxycyclobutyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside
• CAS No.: 905918-14-1
• Molecular Formula: C₃₈H₃₂Cl₂O₁₁
• Molecular Weight: 735.571
• Mol file: 905918-14-1.mol

Synonyms:(1'R,3'S)-2',2'-dichloro-3'-hydroxycyclobutyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside

Chemical Property of (1'R,3'S)-2',2'-dichloro-3'-hydroxycyclobutyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'R,3'S)-2',2'-dichloro-3'-hydroxycyclobutyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside

There total 3 articles about (1'R,3'S)-2',2'-dichloro-3'-hydroxycyclobutyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside 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: 48.0%

vinyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside (905918-05-0) + trifluoroacetyl chloride (76-02-8) → (1'R,3'S)-2',2'-dichloro-3'-hydroxycyclobutyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside (905918-14-1) + (1'S,3'R)-2',2'-dichloro-3'-hydroxycyclobutyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside (905918-13-0)

Guidance literature:

vinyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside; trifluoroacetyl chloride; With copper; zinc; In diethyl ether; at 20 ℃; for 15h;

With sodium tetrahydroborate; In isopropyl alcohol; for 3h; cooling;

DOI:10.1021/jo0600510

Reference yield:

formyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside (98854-00-3) → (1'R,3'S)-2',2'-dichloro-3'-hydroxycyclobutyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside (905918-14-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 64 percent / pyridine / tetrahydrofuran; toluene / -78 - 0 °C

2.1: Zn/Cu / diethyl ether / 15 h / 20 °C

2.2: 17 percent / NaBH₄ / propan-2-ol / 3 h / cooling

With pyridine; copper; zinc; In tetrahydrofuran; diethyl ether; toluene; 1.1: Tebbe olefination;

DOI:10.1021/jo0600510

Reference yield:

2,3,4,6-tetra-O-Bz-β-D-glucopyranosyl bromide (165877-99-6) → (1'R,3'S)-2',2'-dichloro-3'-hydroxycyclobutyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside (905918-14-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 60 percent / AgNO₃ / 1 h / 20 °C

2.1: 64 percent / pyridine / tetrahydrofuran; toluene / -78 - 0 °C

3.1: Zn/Cu / diethyl ether / 15 h / 20 °C

3.2: 17 percent / NaBH₄ / propan-2-ol / 3 h / cooling

With pyridine; copper; silver nitrate; zinc; In tetrahydrofuran; diethyl ether; toluene; 2.1: Tebbe olefination;

DOI:10.1021/jo0600510

upstream raw materials:

vinyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside

trifluoroacetyl chloride

formyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside

2,3,4,6-tetra-O-Bz-β-D-glucopyranosyl bromide