(4S,6R,9aS)-8-Benzyloxymethyl-6-methoxy-4-methyl-5-trimethylsilanyloxy-1,6,7,9a-tetrahydro-4H-benzocycloheptene-6-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (4S,6R,9aS)-8-Benzyloxymethyl-6-methoxy-4-methyl-5-trimethylsilanyloxy-1,6,7,9a-tetrahydro-4H-benzocycloheptene-6-carboxylic acid tert-butyl ester
• CAS No.: 122690-82-8
• Molecular Formula: C₂₉H₄₂O₅Si
• Molecular Weight: 498.735
• Mol file: 122690-82-8.mol

Synonyms:

Chemical Property of (4S,6R,9aS)-8-Benzyloxymethyl-6-methoxy-4-methyl-5-trimethylsilanyloxy-1,6,7,9a-tetrahydro-4H-benzocycloheptene-6-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,6R,9aS)-8-Benzyloxymethyl-6-methoxy-4-methyl-5-trimethylsilanyloxy-1,6,7,9a-tetrahydro-4H-benzocycloheptene-6-carboxylic acid tert-butyl ester

There total 16 articles about (4S,6R,9aS)-8-Benzyloxymethyl-6-methoxy-4-methyl-5-trimethylsilanyloxy-1,6,7,9a-tetrahydro-4H-benzocycloheptene-6-carboxylic acid tert-butyl 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: 87.0%

chloro-trimethyl-silane (75-77-4) + 3-[(1R,2S,6S,7R)-7-(1-Benzyloxymethyl-vinyl)-2-methyl-bicyclo[4.1.0]hept-3-en-1-yl]-2-methoxy-3-oxo-propionic acid tert-butyl ester (122690-80-6,122690-88-4) → (4R,6R,9aR)-8-Benzyloxymethyl-6-methoxy-4-methyl-5-trimethylsilanyloxy-1,6,7,9a-tetrahydro-4H-benzocycloheptene-6-carboxylic acid tert-butyl ester (122690-82-8,122690-83-9) + (4S,6R,9aS)-8-Benzyloxymethyl-6-methoxy-4-methyl-5-trimethylsilanyloxy-1,6,7,9a-tetrahydro-4H-benzocycloheptene-6-carboxylic acid tert-butyl ester (122690-82-8,122690-83-9)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 50 ℃; Yields of byproduct given;

DOI:10.1016/S0040-4039(00)82443-0

Reference yield: 87.0%

chloro-trimethyl-silane (75-77-4) + 3-[(1R,2S,6S,7R)-7-(1-Benzyloxymethyl-vinyl)-2-methyl-bicyclo[4.1.0]hept-3-en-1-yl]-2-methoxy-3-oxo-propionic acid tert-butyl ester (122690-80-6,122690-88-4) → (4R,6R,9aR)-8-Benzyloxymethyl-6-methoxy-4-methyl-5-trimethylsilanyloxy-1,6,7,9a-tetrahydro-4H-benzocycloheptene-6-carboxylic acid tert-butyl ester (122690-82-8,122690-83-9) + (4S,6R,9aS)-8-Benzyloxymethyl-6-methoxy-4-methyl-5-trimethylsilanyloxy-1,6,7,9a-tetrahydro-4H-benzocycloheptene-6-carboxylic acid tert-butyl ester (122690-82-8,122690-83-9)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 50 ℃; Yields of byproduct given;

DOI:10.1016/S0040-4039(00)82443-0

Reference yield:

(+/-)-3c-methyl-cyclohex-4-ene-1r,2c-dicarboxylic acid (15941-50-1,23667-61-0,40469-16-7,40469-17-8,40469-18-9,41792-44-3) → (4R,6R,9aR)-8-Benzyloxymethyl-6-methoxy-4-methyl-5-trimethylsilanyloxy-1,6,7,9a-tetrahydro-4H-benzocycloheptene-6-carboxylic acid tert-butyl ester (122690-82-8,122690-83-9)

Guidance literature:

Multi-step reaction with 8 steps

2: 86 percent / KOMe

3: 87 percent / PCC

4: 72 percent

5: 70 percent / SOCl₂

6: 88 percent / KOtBu

7: 68 percent / LDA

8: NEt₃ / dimethylformamide / 50 °C

With thionyl chloride; potassium methanolate; potassium tert-butylate; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)82443-0

upstream raw materials:

chloro-trimethyl-silane

3-[(1R,2S,6S,7R)-7-(1-Benzyloxymethyl-vinyl)-2-methyl-bicyclo[4.1.0]hept-3-en-1-yl]-2-methoxy-3-oxo-propionic acid tert-butyl ester

(+/-)-3c-methyl-cyclohex-4-ene-1r,2c-dicarboxylic acid

(3aR,7S,7aS)-7-Methyl-3a,4,7,7a-tetrahydro-3H-isobenzofuran-1-one

Downstream raw materials:

(4R,4aR,6R,9aR)-8-Benzyloxymethyl-6-methoxy-4-methyl-5-oxo-1,4a,5,6,7,9a-hexahydro-4H-benzocycloheptene-6-carboxylic acid tert-butyl ester

(4R,4aS,6R,9aR)-8-Benzyloxymethyl-6-methoxy-4-methyl-5-oxo-1,4a,5,6,7,9a-hexahydro-4H-benzocycloheptene-6-carboxylic acid tert-butyl ester