(3S,4S,4aR,6S,7R,8S,9S,9aS)-9-Benzyloxy-6-methoxymethoxymethyl-3,4,8-trimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-one

Base Information

Chemical Name:(3S,4S,4aR,6S,7R,8S,9S,9aS)-9-Benzyloxy-6-methoxymethoxymethyl-3,4,8-trimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-one
CAS No.:157392-49-9
Molecular Formula:C₃₁H₅₂O₇Si
Molecular Weight:564.835
Hs Code.:

(3S,4S,4aR,6S,7R,8S,9S,9aS)-9-Benzyloxy-6-methoxymethoxymethyl-3,4,8-trimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-one

Synonyms:(3S,4S,4aR,6S,7R,8S,9S,9aS)-9-Benzyloxy-6-methoxymethoxymethyl-3,4,8-trimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-one

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Chemical Property of (3S,4S,4aR,6S,7R,8S,9S,9aS)-9-Benzyloxy-6-methoxymethoxymethyl-3,4,8-trimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-one

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Technology Process of (3S,4S,4aR,6S,7R,8S,9S,9aS)-9-Benzyloxy-6-methoxymethoxymethyl-3,4,8-trimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-one

There total 13 articles about (3S,4S,4aR,6S,7R,8S,9S,9aS)-9-Benzyloxy-6-methoxymethoxymethyl-3,4,8-trimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-one 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: 92.0%

: 157220-20-7
(4S,4aR,6S,7R,8S,9S,9aS)-9-Benzyloxy-6-methoxymethoxymethyl-4,8-dimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-one

: 74-88-4
methyl iodide

: 157392-49-9
(3S,4S,4aR,6S,7R,8S,9S,9aS)-9-Benzyloxy-6-methoxymethoxymethyl-3,4,8-trimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-one

Guidance literature:: (4S,4aR,6S,7R,8S,9S,9aS)-9-Benzyloxy-6-methoxymethoxymethyl-4,8-dimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-one; With lithium hexamethyldisilazane; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

methyl iodide; In tetrahydrofuran; hexane; at -78 - 0 ℃;
DOI:10.1021/jo990988j

Reference yield:

: (4S,4aR,6S,7R,8S,9S,9aS)-9-Benzyloxy-6-methoxymethoxymethyl-4,8-dimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-ol

: 157392-49-9
(3S,4S,4aR,6S,7R,8S,9S,9aS)-9-Benzyloxy-6-methoxymethoxymethyl-3,4,8-trimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 6.98 g / pyridinium dichromate; molecular sieves 4A / CH₂Cl₂ / 2 h / 20 °C

2.1: LiHMDS / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 92 percent / tetrahydrofuran; hexane / -78 - 0 °C

With dipyridinium dichromate; 4 A molecular sieve; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; 1.1: Oxidation / 2.1: Metallation / 2.2: Methylation;
DOI:10.1021/jo990988j

Reference yield:

: 157220-15-0
(2R,3S,4S,5S,6R,7S)-4-Benzyloxy-7-methoxymethoxymethyl-5-methyl-2-((S)-1-methyl-allyl)-6-triisopropylsilanyloxy-oxepan-3-ol

: 157392-49-9
(3S,4S,4aR,6S,7R,8S,9S,9aS)-9-Benzyloxy-6-methoxymethoxymethyl-3,4,8-trimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 98 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 2.5 h / 20 °C

2.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 0 - 20 °C

2.2: 9.90 g / hydrogen peroxide; sodium hydroxide / tetrahydrofuran / 1.5 h / 20 °C

3.1: triethylamine; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 0.5 h / 0 °C

4.1: acetic acid / tetrahydrofuran; H₂O / 20 °C

5.1: 6.98 g / pyridinium dichromate; molecular sieves 4A / CH₂Cl₂ / 2 h / 20 °C

6.1: LiHMDS / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.2: 92 percent / tetrahydrofuran; hexane / -78 - 0 °C

With dipyridinium dichromate; pyridine-SO₃ complex; 4 A molecular sieve; pyridinium p-toluenesulfonate; acetic acid; triethylamine; 9-bora-bicyclo[3.3.1]nonane; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; water; dimethyl sulfoxide; 1.1: Addition / 2.1: hydroboration / 2.2: Oxidation / 3.1: Oxidation / 4.1: Hydrolysis / 5.1: Oxidation / 6.1: Metallation / 6.2: Methylation;
DOI:10.1021/jo990988j