(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-(2-[1,3]dithian-2-yl-ethyl)-oxepan-3-ol

Base Information

Chemical Name:(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-(2-[1,3]dithian-2-yl-ethyl)-oxepan-3-ol
CAS No.:908866-11-5
Molecular Formula:C₂₇H₃₆O₄S₂
Molecular Weight:488.712
Hs Code.:

Synonyms:(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-(2-[1,3]dithian-2-yl-ethyl)-oxepan-3-ol

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Chemical Property of (2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-(2-[1,3]dithian-2-yl-ethyl)-oxepan-3-ol

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Technology Process of (2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-(2-[1,3]dithian-2-yl-ethyl)-oxepan-3-ol

There total 8 articles about (2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-(2-[1,3]dithian-2-yl-ethyl)-oxepan-3-ol 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:

: [(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-(2-[1,3]dithian-2-yl-ethyl)-oxepan-3-yloxy]-tert-butyl-dimethyl-silane

: 908866-11-5
(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-(2-[1,3]dithian-2-yl-ethyl)-oxepan-3-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;
DOI:10.1021/ja062524q DOI:10.1021/ja066772y

Reference yield:

: 908866-07-9
(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-hydroxymethyl-oxepan-3-ol

: 908866-11-5
(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-(2-[1,3]dithian-2-yl-ethyl)-oxepan-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

1.2: CH₂Cl₂ / 0.75 h / -78 - 20 °C

2.1: 272.1 mg / CuBr / diethyl ether / 1 h / 0 °C

3.1: OsO₄; aq. 4-methylmorpholine N-oxide / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h / 20 °C

3.2: NaIO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h / 20 °C

4.1: BF₃*OEt₂ / CH₂Cl₂ / 0.67 h / -78 - 0 °C

5.1: 1.39 g / TBAF / tetrahydrofuran / 20 °C

With 2,6-dimethylpyridine; osmium(VIII) oxide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; 4-methylmorpholine N-oxide; copper(I) bromide; In tetrahydrofuran; diethyl ether; dichloromethane; tert-butyl alcohol;
DOI:10.1021/ja066772y

Reference yield:

: 850656-74-5
((2R,4aR,6S,7R,9aS)-7-Benzyloxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-methanol

: 908866-11-5
(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-(2-[1,3]dithian-2-yl-ethyl)-oxepan-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaH / dimethylformamide; tetrahydrofuran / 0.5 h / 20 °C

1.2: tetrahydrofuran; dimethylformamide / 1 h / 20 °C

2.1: 9.10 g / CSA / methanol; CHCl₃ / 20 °C

3.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

3.2: CH₂Cl₂ / 0.75 h / -78 - 20 °C

4.1: 272.1 mg / CuBr / diethyl ether / 1 h / 0 °C

5.1: OsO₄; aq. 4-methylmorpholine N-oxide / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h / 20 °C

5.2: NaIO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h / 20 °C

6.1: BF₃*OEt₂ / CH₂Cl₂ / 0.67 h / -78 - 0 °C

7.1: 1.39 g / TBAF / tetrahydrofuran / 20 °C

With 2,6-dimethylpyridine; osmium(VIII) oxide; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydride; 4-methylmorpholine N-oxide; copper(I) bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/ja066772y