{(1R,3S,5R,6R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-hydroxy-8,8-dimethyl-7-oxo-2,9-dioxa-bicyclo[3.3.1]non-1-yl}-acetic acid ethyl ester

Base Information

Chemical Name:{(1R,3S,5R,6R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-hydroxy-8,8-dimethyl-7-oxo-2,9-dioxa-bicyclo[3.3.1]non-1-yl}-acetic acid ethyl ester
CAS No.:794587-08-9
Molecular Formula:C₃₁H₄₂O₇Si
Molecular Weight:554.756
Hs Code.:

Synonyms:{(1R,3S,5R,6R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-hydroxy-8,8-dimethyl-7-oxo-2,9-dioxa-bicyclo[3.3.1]non-1-yl}-acetic acid ethyl ester

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Chemical Property of {(1R,3S,5R,6R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-hydroxy-8,8-dimethyl-7-oxo-2,9-dioxa-bicyclo[3.3.1]non-1-yl}-acetic acid ethyl ester

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Technology Process of {(1R,3S,5R,6R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-hydroxy-8,8-dimethyl-7-oxo-2,9-dioxa-bicyclo[3.3.1]non-1-yl}-acetic acid ethyl ester

There total 8 articles about {(1R,3S,5R,6R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-hydroxy-8,8-dimethyl-7-oxo-2,9-dioxa-bicyclo[3.3.1]non-1-yl}-acetic acid ethyl 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: 80.0%

: 794587-07-8
{(1R,3S,5R,6S,7S)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6,7-dihydroxy-8,8-dimethyl-2,9-dioxa-bicyclo[3.3.1]non-1-yl}-acetic acid ethyl ester

: 794587-08-9
{(1R,3S,5R,6R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-hydroxy-8,8-dimethyl-7-oxo-2,9-dioxa-bicyclo[3.3.1]non-1-yl}-acetic acid ethyl ester

: {(1R,3S,5R,7S)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-7-hydroxy-8,8-dimethyl-6-oxo-2,9-dioxa-bicyclo[3.3.1]non-1-yl}-acetic acid ethyl ester

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - 20 ℃; for 1.5h;
DOI:10.1021/ol0483044

Reference yield:

: 66248-79-1
ethyl 4,4-dimethyl-3-oxo-hex-5-enoate

: 794587-08-9
{(1R,3S,5R,6R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-hydroxy-8,8-dimethyl-7-oxo-2,9-dioxa-bicyclo[3.3.1]non-1-yl}-acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 72 percent / i-Pr₂NEt / acetonitrile; methanol; hexane / 24 h / 20 °C

2.1: 87 percent / camphorsulfonic acid / benzene / 1 h / Heating

3.1: 93 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 11 h / 20 °C

4.1: 2-methyl-2-butene; BH₃ / tetrahydrofuran / 3 h / 0 °C

4.2: 91 percent / NaBO₃*4H₂O / tetrahydrofuran; H₂O / 1 h / 20 °C

5.1: 99 percent / imidazole / dimethylformamide / 2 h / 20 °C

6.1: 97 percent / citric acid monohydrate; OsO₄; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H₂O / 8 h / 20 °C

7.1: 80 percent / oxalyl chloride; DMSO; i-Pr₂NEt / CH₂Cl₂ / 1.5 h / -78 - 20 °C

With 1H-imidazole; osmium(VIII) oxide; 2-methyl-but-2-ene; oxalyl dichloride; camphor-10-sulfonic acid; borane; dimethyl sulfoxide; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; citric acid; Grubbs catalyst first generation; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene; 6.1: Sharpless dihydroxylation / 7.1: Swern oxidation;
DOI:10.1021/ol0483044

Reference yield:

: (3R,5R)-hepta-1,6-diene-3,5-diol

: 794587-08-9
{(1R,3S,5R,6R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-hydroxy-8,8-dimethyl-7-oxo-2,9-dioxa-bicyclo[3.3.1]non-1-yl}-acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 87 percent / camphorsulfonic acid / benzene / 1 h / Heating

2.1: 93 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 11 h / 20 °C

3.1: 2-methyl-2-butene; BH₃ / tetrahydrofuran / 3 h / 0 °C

3.2: 91 percent / NaBO₃*4H₂O / tetrahydrofuran; H₂O / 1 h / 20 °C

4.1: 99 percent / imidazole / dimethylformamide / 2 h / 20 °C

5.1: 97 percent / citric acid monohydrate; OsO₄; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H₂O / 8 h / 20 °C

6.1: 80 percent / oxalyl chloride; DMSO; i-Pr₂NEt / CH₂Cl₂ / 1.5 h / -78 - 20 °C

With 1H-imidazole; osmium(VIII) oxide; 2-methyl-but-2-ene; oxalyl dichloride; camphor-10-sulfonic acid; borane; dimethyl sulfoxide; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; citric acid; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 5.1: Sharpless dihydroxylation / 6.1: Swern oxidation;
DOI:10.1021/ol0483044