Acetic acid (1S,4S,4aR,6S,8R,8aS)-2-acetoxymethyl-6-(tert-butyl-diphenyl-silanyloxy)-4-((R)-1-formyl-2-methyl-propyl)-8-((S)-1-methyl-2-oxo-ethyl)-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl ester

Base Information

Chemical Name:Acetic acid (1S,4S,4aR,6S,8R,8aS)-2-acetoxymethyl-6-(tert-butyl-diphenyl-silanyloxy)-4-((R)-1-formyl-2-methyl-propyl)-8-((S)-1-methyl-2-oxo-ethyl)-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl ester
CAS No.:832111-85-0
Molecular Formula:C₃₉H₅₂O₇Si
Molecular Weight:660.923
Hs Code.:

Acetic acid (1S,4S,4aR,6S,8R,8aS)-2-acetoxymethyl-6-(tert-butyl-diphenyl-silanyloxy)-4-((R)-1-formyl-2-methyl-propyl)-8-((S)-1-methyl-2-oxo-ethyl)-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl ester

Synonyms:Acetic acid (1S,4S,4aR,6S,8R,8aS)-2-acetoxymethyl-6-(tert-butyl-diphenyl-silanyloxy)-4-((R)-1-formyl-2-methyl-propyl)-8-((S)-1-methyl-2-oxo-ethyl)-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl ester

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Chemical Property of Acetic acid (1S,4S,4aR,6S,8R,8aS)-2-acetoxymethyl-6-(tert-butyl-diphenyl-silanyloxy)-4-((R)-1-formyl-2-methyl-propyl)-8-((S)-1-methyl-2-oxo-ethyl)-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl ester

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Technology Process of Acetic acid (1S,4S,4aR,6S,8R,8aS)-2-acetoxymethyl-6-(tert-butyl-diphenyl-silanyloxy)-4-((R)-1-formyl-2-methyl-propyl)-8-((S)-1-methyl-2-oxo-ethyl)-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl ester

There total 8 articles about Acetic acid (1S,4S,4aR,6S,8R,8aS)-2-acetoxymethyl-6-(tert-butyl-diphenyl-silanyloxy)-4-((R)-1-formyl-2-methyl-propyl)-8-((S)-1-methyl-2-oxo-ethyl)-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl 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: 97.0%

: 832111-84-9
Acetic acid (1S,4S,4aR,6S,8S,8aS)-2-acetoxymethyl-6-(tert-butyl-diphenyl-silanyloxy)-8-((S)-2-hydroxy-1-methyl-ethyl)-4-((R)-1-hydroxymethyl-2-methyl-propyl)-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl ester

: 832111-85-0
Acetic acid (1S,4S,4aR,6S,8R,8aS)-2-acetoxymethyl-6-(tert-butyl-diphenyl-silanyloxy)-4-((R)-1-formyl-2-methyl-propyl)-8-((S)-1-methyl-2-oxo-ethyl)-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl ester

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - -40 ℃; for 4h;
DOI:10.1021/jo048458x

Reference yield:

: (1R,3S,4aR,5R,8aS)-1-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-5-[(R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-3-(tert-butyl-diphenyl-silanyloxy)-7-methyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

: 832111-85-0
Acetic acid (1S,4S,4aR,6S,8R,8aS)-2-acetoxymethyl-6-(tert-butyl-diphenyl-silanyloxy)-4-((R)-1-formyl-2-methyl-propyl)-8-((S)-1-methyl-2-oxo-ethyl)-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 98 percent / Na₂HPO₄; m-CPBA / CH₂Cl₂ / 0.33 h / 0 °C

2: 98 percent / 2,2,6,6-tetramethylpiperidine; n-BuLi; AlClMe₂ / benzene; hexane / 2 h / 0 °C

3: 96 percent / pyridine; DMAP / 16 h / 20 °C

4: 69 percent / SeO₂; tert-butyl hydroperoxide / CH₂Cl₂ / 20 h / 20 °C

5: 67 percent / methanesulfonyl chloride; Et₃N / tetrahydrofuran / 8 h / -78 - 0 °C

6: 92 percent / acetone / 48 h / Heating

7: 83 percent / TsOH / methanol; tetrahydrofuran / 24 h / 20 °C

8: 97 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 4 h / -78 - -40 °C

With pyridine; 2,2,6,6-tetramethyl-piperidine; tert.-butylhydroperoxide; dmap; disodium hydrogenphosphate; n-butyllithium; selenium(IV) oxide; oxalyl dichloride; dimethylaluminum chloride; toluene-4-sulfonic acid; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; acetone; benzene; 8: Swern oxidation;
DOI:10.1021/jo048458x

Reference yield:

: 832111-72-5
(1aR,3R,3aR,5S,7S,7aS,7bS)-7-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-3-[(R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-5-(tert-butyl-diphenyl-silanyloxy)-1a-methyl-decahydro-1-oxa-cyclopropa[a]naphthalene

: 832111-85-0
Acetic acid (1S,4S,4aR,6S,8R,8aS)-2-acetoxymethyl-6-(tert-butyl-diphenyl-silanyloxy)-4-((R)-1-formyl-2-methyl-propyl)-8-((S)-1-methyl-2-oxo-ethyl)-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 98 percent / 2,2,6,6-tetramethylpiperidine; n-BuLi; AlClMe₂ / benzene; hexane / 2 h / 0 °C

2: 96 percent / pyridine; DMAP / 16 h / 20 °C

3: 69 percent / SeO₂; tert-butyl hydroperoxide / CH₂Cl₂ / 20 h / 20 °C

4: 67 percent / methanesulfonyl chloride; Et₃N / tetrahydrofuran / 8 h / -78 - 0 °C

5: 92 percent / acetone / 48 h / Heating

6: 83 percent / TsOH / methanol; tetrahydrofuran / 24 h / 20 °C

7: 97 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 4 h / -78 - -40 °C

With pyridine; 2,2,6,6-tetramethyl-piperidine; tert.-butylhydroperoxide; dmap; n-butyllithium; selenium(IV) oxide; oxalyl dichloride; dimethylaluminum chloride; toluene-4-sulfonic acid; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; acetone; benzene; 7: Swern oxidation;
DOI:10.1021/jo048458x