(3R,4S,5R,7R)-3-O-benzyl-4,5-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-7-benzyloxymethyl-thiepane-3,4,5-triol

Base Information

Chemical Name:(3R,4S,5R,7R)-3-O-benzyl-4,5-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-7-benzyloxymethyl-thiepane-3,4,5-triol
CAS No.:1422183-87-6
Molecular Formula:C₂₇H₃₆O₆S
Molecular Weight:488.645
Hs Code.:

Synonyms:(3R,4S,5R,7R)-3-O-benzyl-4,5-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-7-benzyloxymethyl-thiepane-3,4,5-triol

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Chemical Property of (3R,4S,5R,7R)-3-O-benzyl-4,5-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-7-benzyloxymethyl-thiepane-3,4,5-triol

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Technology Process of (3R,4S,5R,7R)-3-O-benzyl-4,5-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-7-benzyloxymethyl-thiepane-3,4,5-triol

There total 3 articles about (3R,4S,5R,7R)-3-O-benzyl-4,5-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-7-benzyloxymethyl-thiepane-3,4,5-triol 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:

: 1422183-83-2
(2S,3S,4R,6S)-2,7-O-bisbenzyl-3,4-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-heptane-1,2,3,4,6,7-hexaol

: 1422183-87-6
(3R,4S,5R,7R)-3-O-benzyl-4,5-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-7-benzyloxymethyl-thiepane-3,4,5-triol

Guidance literature:: (2S,3S,4R,6S)-2,7-O-bisbenzyl-3,4-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-heptane-1,2,3,4,6,7-hexaol; With methanesulfonyl chloride; In pyridine; at 0 ℃; for 0.5h;

With sodium sulfide; 15-crown-5; In ethanol; at 2 ℃; Reflux;
DOI:10.1016/j.tet.2012.12.047

Reference yield:

: (1S,2S,3R,4S,5S)-3,7-O-bisbenzyl-1,2-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-cyclohexane-4,5-diol

: 1422183-87-6
(3R,4S,5R,7R)-3-O-benzyl-4,5-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-7-benzyloxymethyl-thiepane-3,4,5-triol

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium periodate; sodium tetrahydroborate

2.1: methanesulfonyl chloride / pyridine / 0.5 h / 0 °C

2.2: 2 °C / Reflux

With sodium tetrahydroborate; sodium periodate; methanesulfonyl chloride; In pyridine;
DOI:10.1016/j.tet.2012.12.047

Reference yield:

: C₂₃H₃₂O₅

: 1422183-87-6
(3R,4S,5R,7R)-3-O-benzyl-4,5-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-7-benzyloxymethyl-thiepane-3,4,5-triol

Guidance literature:: Multi-step reaction with 3 steps

1.1: pyridine; 4-methylmorpholine N-oxide; osmium(VIII) oxide / tert-butyl alcohol; water; tetrahydrofuran / 19 h / 100 °C

2.1: sodium periodate; sodium tetrahydroborate

3.1: methanesulfonyl chloride / pyridine / 0.5 h / 0 °C

3.2: 2 °C / Reflux

With pyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; methanesulfonyl chloride; 4-methylmorpholine N-oxide; In tetrahydrofuran; pyridine; water; tert-butyl alcohol;
DOI:10.1016/j.tet.2012.12.047