(S)-1-[(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyl]-2-ethoxy-prop-2-en-1-ol

Base Information

• Chemical Name: (S)-1-[(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyl]-2-ethoxy-prop-2-en-1-ol
• CAS No.: 663605-90-1
• Molecular Formula: C₃₄H₅₀O₅Si
• Molecular Weight: 566.853
• Mol file: 663605-90-1.mol

Synonyms:(S)-1-[(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyl]-2-ethoxy-prop-2-en-1-ol

Chemical Property of (S)-1-[(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyl]-2-ethoxy-prop-2-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-1-[(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyl]-2-ethoxy-prop-2-en-1-ol

There total 18 articles about (S)-1-[(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyl]-2-ethoxy-prop-2-en-1-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: 96.0%

ethyl vinyl ether (109-92-2,25104-37-4) + (1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentanecarbaldehyde (663606-11-9) → (S)-1-[(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyl]-2-ethoxy-prop-2-en-1-ol (663605-90-1) + (R)-1-[(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyl]-2-ethoxy-prop-2-en-1-ol

Guidance literature:

With tert.-butyl lithium; In tetrahydrofuran; at -78 ℃;

DOI:10.1002/anie.200353140

Reference yield:

(1S,2R,3S,5S)-5-Isopropenyl-2-methyl-3-(tetrahydro-pyran-2-yloxy)-cyclopentanecarboxylic acid methyl ester (156714-42-0) → (S)-1-[(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyl]-2-ethoxy-prop-2-en-1-ol (663605-90-1) + (R)-1-[(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyl]-2-ethoxy-prop-2-en-1-ol

Guidance literature:

Multi-step reaction with 11 steps

1: pyridinium p-toluenesulfonate / methanol / 40 °C

2: 1H-imidazole / N,N-dimethyl-formamide / 20 °C

3: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C

4: sodium hydride / N,N-dimethyl-formamide / 20 °C

5: osmium(VIII) oxide; N-methyl-2-indolinone; water / acetone / 20 °C

6: sodium periodate / 20 °C

7: tetrahydrofuran / -78 °C

8: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

9: phosphate buffer; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 20 °C / pH 7

10: N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve / dichloromethane / 20 °C

11: tert.-butyl lithium / tetrahydrofuran / -78 °C

With 1H-imidazole; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; phosphate buffer; tetrapropylammonium perruthennate; 4 A molecular sieve; water; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydride; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1002/anie.200353140

Reference yield:

(2R,3S,5S)-2-Chloro-5-isopropenyl-2-methyl-3-(tetrahydro-pyran-2-yloxy)-cyclohexanone (156629-27-5) → (S)-1-[(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyl]-2-ethoxy-prop-2-en-1-ol (663605-90-1) + (R)-1-[(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyl]-2-ethoxy-prop-2-en-1-ol

Guidance literature:

Multi-step reaction with 12 steps

1: sodium methylate / 0 °C

2: pyridinium p-toluenesulfonate / methanol / 40 °C

3: 1H-imidazole / N,N-dimethyl-formamide / 20 °C

4: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C

5: sodium hydride / N,N-dimethyl-formamide / 20 °C

6: osmium(VIII) oxide; N-methyl-2-indolinone; water / acetone / 20 °C

7: sodium periodate / 20 °C

8: tetrahydrofuran / -78 °C

9: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

10: phosphate buffer; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 20 °C / pH 7

11: N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve / dichloromethane / 20 °C

12: tert.-butyl lithium / tetrahydrofuran / -78 °C

With 1H-imidazole; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; phosphate buffer; tetrapropylammonium perruthennate; 4 A molecular sieve; water; tert.-butyl lithium; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; 1: Favorskii rearrangement;

DOI:10.1002/anie.200353140

upstream raw materials:

ethyl vinyl ether

(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentanecarbaldehyde

[(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyl]-methanol

tert-Butyl-[(1S,2R,3R,4S)-3-(4-methoxy-benzyloxymethyl)-4-(1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyloxy]-diphenyl-silane

Downstream raw materials:

C₄₀H₆₄O₅Si₂

Acetic acid (R)-2-[(2S,3R,3aR,4S,5R,6S,8S,8aS)-2-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-6,8-bis-methoxymethoxy-3,8-dimethyl-4-triethylsilanyloxy-decahydro-azulen-5-yl]-2-hydroxy-propyl ester

2-(Diethoxy-phosphoryl)-propionic acid (1R,2S,3aS,4S,6S,8S,8aR)-2-(tert-butyl-diphenyl-silanyloxy)-4-methoxymethoxy-1,4-dimethyl-7-oxo-8-triethylsilanyloxy-decahydro-azulen-6-yl ester

(4S,4aR,5R,6S,7aS,8S,9aS)-6-(tert-Butyl-diphenyl-silanyloxy)-8-methoxymethoxy-3,5,8-trimethyl-4-triethylsilanyloxy-4a,5,6,7,7a,8,9,9a-octahydro-4H-azuleno[6,5-b]furan-2-one

Refernces

• 1、 Oliver, Steven F.,Hoegenauer, Klemens,Simic, Oliver,Antonello, Alessandra,Smith, Martin D.,Ley, Steven V.. "A Route to the Thapsigargins from (S)-Carvone Providing a Substrate-Controlled Total Synthesis of Trilobolide, Nortrilobolide, and Thapsivillosin F". . p. 5996 - 6000. Retrieved 2007/10/03.