((2R,3S,5aR,7S,8R,10aS)-8-Benzyloxy-7-benzyloxymethyl-3-hydroxy-3-methyl-decahydro-1,6-dioxa-heptalen-2-yl)-acetic acid methyl ester

Base Information

Chemical Name:((2R,3S,5aR,7S,8R,10aS)-8-Benzyloxy-7-benzyloxymethyl-3-hydroxy-3-methyl-decahydro-1,6-dioxa-heptalen-2-yl)-acetic acid methyl ester
CAS No.:924656-40-6
Molecular Formula:C₂₉H₃₈O₇
Molecular Weight:498.617
Hs Code.:

Synonyms:((2R,3S,5aR,7S,8R,10aS)-8-Benzyloxy-7-benzyloxymethyl-3-hydroxy-3-methyl-decahydro-1,6-dioxa-heptalen-2-yl)-acetic acid methyl ester

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Chemical Property of ((2R,3S,5aR,7S,8R,10aS)-8-Benzyloxy-7-benzyloxymethyl-3-hydroxy-3-methyl-decahydro-1,6-dioxa-heptalen-2-yl)-acetic acid methyl ester

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Technology Process of ((2R,3S,5aR,7S,8R,10aS)-8-Benzyloxy-7-benzyloxymethyl-3-hydroxy-3-methyl-decahydro-1,6-dioxa-heptalen-2-yl)-acetic acid methyl ester

There total 8 articles about ((2R,3S,5aR,7S,8R,10aS)-8-Benzyloxy-7-benzyloxymethyl-3-hydroxy-3-methyl-decahydro-1,6-dioxa-heptalen-2-yl)-acetic acid methyl 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: 57.0%

: 924656-38-2
(E)-3-[(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-(3-oxo-butyl)-oxepan-3-yloxy]-acrylic acid methyl ester

: 924656-39-3
(1S,3R,7S,10R,12S,13R)-13-Benzyloxy-12-benzyloxymethyl-7-methyl-2,6,11-trioxa-tricyclo[8.5.0.0^3,7]pentadecan-5-one

: 924656-40-6
((2R,3S,5aR,7S,8R,10aS)-8-Benzyloxy-7-benzyloxymethyl-3-hydroxy-3-methyl-decahydro-1,6-dioxa-heptalen-2-yl)-acetic acid methyl ester

Guidance literature:: With methanol; samarium diiodide; In tetrahydrofuran; at 20 ℃; for 0.5h;
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

: 924656-40-6
((2R,3S,5aR,7S,8R,10aS)-8-Benzyloxy-7-benzyloxymethyl-3-hydroxy-3-methyl-decahydro-1,6-dioxa-heptalen-2-yl)-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 8 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: 92 percent / PdCl₂; O₂; Cu(OAc)2 / H₂O; N,N-dimethyl-acetamide / 36 h / 20 °C

6.1: TBAF / tetrahydrofuran / 2.5 h / 20 °C

7.1: 178.3 mg / 4-methylmorpholine / CH₂Cl₂ / 20 °C

8.1: 37 percent / SmI₂; MeOH / tetrahydrofuran / 0.5 h / 20 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; methanol; samarium diiodide; copper diacetate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; oxygen; sodium hydride; copper(I) bromide; palladium dichloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide; 5.1: Wacker-Tsuji reaction;
DOI:10.1021/ja066772y

Reference yield:

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

: 924656-40-6
((2R,3S,5aR,7S,8R,10aS)-8-Benzyloxy-7-benzyloxymethyl-3-hydroxy-3-methyl-decahydro-1,6-dioxa-heptalen-2-yl)-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 6 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: 92 percent / PdCl₂; O₂; Cu(OAc)2 / H₂O; N,N-dimethyl-acetamide / 36 h / 20 °C

4.1: TBAF / tetrahydrofuran / 2.5 h / 20 °C

5.1: 178.3 mg / 4-methylmorpholine / CH₂Cl₂ / 20 °C

6.1: 37 percent / SmI₂; MeOH / tetrahydrofuran / 0.5 h / 20 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; methanol; samarium diiodide; copper diacetate; tetrabutyl ammonium fluoride; oxygen; copper(I) bromide; palladium dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl acetamide; water; 3.1: Wacker-Tsuji reaction;
DOI:10.1021/ja066772y