((2R,3S,5aR,7S,8R,10aS)-2-Allyl-8-benzyloxy-7-benzyloxymethyl-3-methyl-decahydro-1,6-dioxa-heptalen-3-yloxy)-tert-butyl-dimethyl-silane

Base Information

Chemical Name:((2R,3S,5aR,7S,8R,10aS)-2-Allyl-8-benzyloxy-7-benzyloxymethyl-3-methyl-decahydro-1,6-dioxa-heptalen-3-yloxy)-tert-butyl-dimethyl-silane
CAS No.:924656-43-9
Molecular Formula:C₃₅H₅₂O₅Si
Molecular Weight:580.88
Hs Code.:

Synonyms:((2R,3S,5aR,7S,8R,10aS)-2-Allyl-8-benzyloxy-7-benzyloxymethyl-3-methyl-decahydro-1,6-dioxa-heptalen-3-yloxy)-tert-butyl-dimethyl-silane

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Chemical Property of ((2R,3S,5aR,7S,8R,10aS)-2-Allyl-8-benzyloxy-7-benzyloxymethyl-3-methyl-decahydro-1,6-dioxa-heptalen-3-yloxy)-tert-butyl-dimethyl-silane

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Technology Process of ((2R,3S,5aR,7S,8R,10aS)-2-Allyl-8-benzyloxy-7-benzyloxymethyl-3-methyl-decahydro-1,6-dioxa-heptalen-3-yloxy)-tert-butyl-dimethyl-silane

There total 15 articles about ((2R,3S,5aR,7S,8R,10aS)-2-Allyl-8-benzyloxy-7-benzyloxymethyl-3-methyl-decahydro-1,6-dioxa-heptalen-3-yloxy)-tert-butyl-dimethyl-silane 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,5aR,7S,8R,10aS)-8-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-decahydro-1,6-dioxa-heptalen-2-yl]-acetaldehyde

: 1779-49-3
Methyltriphenylphosphonium bromide

: 924656-43-9
((2R,3S,5aR,7S,8R,10aS)-2-Allyl-8-benzyloxy-7-benzyloxymethyl-3-methyl-decahydro-1,6-dioxa-heptalen-3-yloxy)-tert-butyl-dimethyl-silane

Guidance literature:: Methyltriphenylphosphonium bromide; With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 0.5h;

[(2R,3S,5aR,7S,8R,10aS)-8-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-decahydro-1,6-dioxa-heptalen-2-yl]-acetaldehyde; In tetrahydrofuran; at 0 ℃; for 0.5h;
DOI:10.1021/ja066772y

Reference yield:

: (2R,4aR,6S,7R,9aS)-7-Benzyloxy-6-benzyloxymethyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocycloheptene

: 924656-43-9
((2R,3S,5aR,7S,8R,10aS)-2-Allyl-8-benzyloxy-7-benzyloxymethyl-3-methyl-decahydro-1,6-dioxa-heptalen-3-yloxy)-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 12 steps

1.1: 9.10 g / CSA / methanol; CHCl₃ / 20 °C

2.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

2.2: CH₂Cl₂ / 0.75 h / -78 - 20 °C

3.1: 272.1 mg / CuBr / diethyl ether / 1 h / 0 °C

4.1: 92 percent / PdCl₂; O₂; Cu(OAc)2 / H₂O; N,N-dimethyl-acetamide / 36 h / 20 °C

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

6.1: 178.3 mg / 4-methylmorpholine / CH₂Cl₂ / 20 °C

7.1: 57 percent / SmI₂; MeOH / tetrahydrofuran / 0.5 h / 20 °C

8.1: 100 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

9.1: Et₃N / CH₂Cl₂ / 3 h / 20 °C

10.1: 254.8 mg / CSA / methanol; CH₂Cl₂ / 1 h / 0 °C

11.1: SO₃*pyridine; Et₃N / CH₂Cl₂; dimethylsulfoxide / 1 h / 0 °C

12.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

12.2: 265.9 mg / tetrahydrofuran / 0.5 h / 0 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; methanol; lithium aluminium tetrahydride; samarium diiodide; copper diacetate; pyridine-SO₃ complex; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; oxygen; sodium hexamethyldisilazane; triethylamine; copper(I) bromide; palladium dichloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; N,N-dimethyl acetamide; water; dimethyl sulfoxide; 4.1: Wacker-Tsuji reaction / 12.2: Wittig reaction;
DOI:10.1021/ja066772y

Reference yield:

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

: 924656-43-9
((2R,3S,5aR,7S,8R,10aS)-2-Allyl-8-benzyloxy-7-benzyloxymethyl-3-methyl-decahydro-1,6-dioxa-heptalen-3-yloxy)-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 11 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: 57 percent / SmI₂; MeOH / tetrahydrofuran / 0.5 h / 20 °C

7.1: 100 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

8.1: Et₃N / CH₂Cl₂ / 3 h / 20 °C

9.1: 254.8 mg / CSA / methanol; CH₂Cl₂ / 1 h / 0 °C

10.1: SO₃*pyridine; Et₃N / CH₂Cl₂; dimethylsulfoxide / 1 h / 0 °C

11.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

11.2: 265.9 mg / tetrahydrofuran / 0.5 h / 0 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; methanol; lithium aluminium tetrahydride; samarium diiodide; copper diacetate; pyridine-SO₃ complex; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; oxygen; sodium hexamethyldisilazane; triethylamine; copper(I) bromide; palladium dichloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl acetamide; water; dimethyl sulfoxide; 3.1: Wacker-Tsuji reaction / 11.2: Wittig reaction;
DOI:10.1021/ja066772y