(2R,3R,4R,5S,6S)-acetic acid 4,5-diacetoxy-2-acetoxymethyl-6-(3-bromophenyl)tetrahydropyran-3-yl ester

Base Information

Chemical Name:(2R,3R,4R,5S,6S)-acetic acid 4,5-diacetoxy-2-acetoxymethyl-6-(3-bromophenyl)tetrahydropyran-3-yl ester
CAS No.:655237-66-4
Molecular Formula:C₂₀H₂₃BrO₉
Molecular Weight:487.301
Hs Code.:

Synonyms:(2R,3R,4R,5S,6S)-acetic acid 4,5-diacetoxy-2-acetoxymethyl-6-(3-bromophenyl)tetrahydropyran-3-yl ester

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Chemical Property of (2R,3R,4R,5S,6S)-acetic acid 4,5-diacetoxy-2-acetoxymethyl-6-(3-bromophenyl)tetrahydropyran-3-yl ester

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Technology Process of (2R,3R,4R,5S,6S)-acetic acid 4,5-diacetoxy-2-acetoxymethyl-6-(3-bromophenyl)tetrahydropyran-3-yl ester

There total 7 articles about (2R,3R,4R,5S,6S)-acetic acid 4,5-diacetoxy-2-acetoxymethyl-6-(3-bromophenyl)tetrahydropyran-3-yl ester 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: 83.0%

: 591-18-4
1-Bromo-3-iodobenzene

: 572-09-8
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

: 655237-66-4
(2R,3R,4R,5S,6S)-acetic acid 4,5-diacetoxy-2-acetoxymethyl-6-(3-bromophenyl)tetrahydropyran-3-yl ester

Guidance literature:: With bis(acetylacetonate)nickel(II); magnesium chloride; In tetrahydrofuran; at 15 ℃; stereoselective reaction;
DOI:10.1007/s11426-019-9501-4

Reference yield: 45.0%

: 108-36-1
1,3-dibromobenzene

: 108-24-7
acetic anhydride

: 572-09-8
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

: 655237-66-4
(2R,3R,4R,5S,6S)-acetic acid 4,5-diacetoxy-2-acetoxymethyl-6-(3-bromophenyl)tetrahydropyran-3-yl ester

Guidance literature:: 1,3-dibromobenzene; With magnesium; ethylene dibromide; In diethyl ether; Heating / reflux;

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide; In diethyl ether; for 5h; Heating / reflux;

acetic anhydride; With pyridine; acetic acid; more than 3 stages;

Reference yield:

: C₆H₄BrIZn*ClLi

: 572-09-8
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

: 655237-66-4
(2R,3R,4R,5S,6S)-acetic acid 4,5-diacetoxy-2-acetoxymethyl-6-(3-bromophenyl)tetrahydropyran-3-yl ester

: (2R,3R,4R,5S,6R)-acetic acid 4,5-diacetoxy-2-acetoxymethyl-6-(3-bromophenyl)tetrahydropyran-3-yl ester

Guidance literature:: With bis (1,5-cyclopentadiene)nickel ⁽⁰⁾; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine; In N,N-dimethyl-formamide; at 25 ℃; for 12h; optical yield given as %de;
DOI:10.1021/ja8041564