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

Base Information

Chemical Name:(1'S,3'R)-2',2'-dichloro-3'-hydroxycyclobutyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside
CAS No.:905918-13-0
Molecular Formula:C₃₈H₃₂Cl₂O₁₁
Molecular Weight:735.571
Hs Code.:

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

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

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

There total 3 articles about (1'S,3'R)-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%

: 905918-05-0
vinyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside

: 76-02-8
trifluoroacetyl chloride

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

: 905918-13-0
(1'S,3'R)-2',2'-dichloro-3'-hydroxycyclobutyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside

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:

: 98854-00-3
formyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside

: 905918-13-0
(1'S,3'R)-2',2'-dichloro-3'-hydroxycyclobutyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside

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: 48 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:

: 165877-99-6
2,3,4,6-tetra-O-Bz-β-D-glucopyranosyl bromide

: 905918-13-0
(1'S,3'R)-2',2'-dichloro-3'-hydroxycyclobutyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside

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: 48 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