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

Base Information

Chemical Name:(2R,3S,4S,4aR,6S,7R,8S,9S,9aS)-2-Allyl-9-benzyloxy-6-methoxymethoxymethyl-3,4,8-trimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-ol
CAS No.:157220-21-8
Molecular Formula:C₃₄H₅₈O₇Si
Molecular Weight:606.916
Hs Code.:

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

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

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

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

There total 14 articles about (2R,3S,4S,4aR,6S,7R,8S,9S,9aS)-2-Allyl-9-benzyloxy-6-methoxymethoxymethyl-3,4,8-trimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-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: 79.0%

: 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

: 1730-25-2
allylmagnesium bromide

: 157220-21-8
(2R,3S,4S,4aR,6S,7R,8S,9S,9aS)-2-Allyl-9-benzyloxy-6-methoxymethoxymethyl-3,4,8-trimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-ol

Guidance literature:: In tetrahydrofuran; at -78 ℃;
DOI:10.1021/jo00083a008

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

: 157220-21-8
(2R,3S,4S,4aR,6S,7R,8S,9S,9aS)-2-Allyl-9-benzyloxy-6-methoxymethoxymethyl-3,4,8-trimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-ol

Guidance literature:: Multi-step reaction with 3 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

3.1: 79 percent / tetrahydrofuran; diethyl ether / 0.75 h / -78 °C

With dipyridinium dichromate; 4 A molecular sieve; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1.1: Oxidation / 2.1: Metallation / 2.2: Methylation / 3.1: Addition;
DOI:10.1021/jo990988j

Reference yield:

: 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

: 157220-21-8
(2R,3S,4S,4aR,6S,7R,8S,9S,9aS)-2-Allyl-9-benzyloxy-6-methoxymethoxymethyl-3,4,8-trimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-ol

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: 92 percent / tetrahydrofuran; hexane / -78 - 0 °C

2.1: 79 percent / tetrahydrofuran; diethyl ether / 0.75 h / -78 °C

With lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; hexane; 1.1: Metallation / 1.2: Methylation / 2.1: Addition;
DOI:10.1021/jo990988j