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

Base Information

• Chemical Name: [(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyl]-methanol
• CAS No.: 663605-89-8
• Molecular Formula: C₃₀H₄₄O₄Si
• Molecular Weight: 496.762
• Mol file: 663605-89-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about [(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyl]-methanol 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:

tert-Butyl-[(1S,2R,3R,4S)-3-(4-methoxy-benzyloxymethyl)-4-(1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyloxy]-diphenyl-silane (663605-88-7) → [(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyl]-methanol (663605-89-8) + [(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((R)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyl]-methanol (663606-08-4)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In phosphate buffer; dichloromethane; at 20 ℃; for 0.5h; pH=7;

DOI:10.1002/chem.200700302

Reference yield:

(2R,3S,5S)-2-Chloro-5-isopropenyl-2-methyl-3-(tetrahydro-pyran-2-yloxy)-cyclohexanone (156629-27-5) → [(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyl]-methanol (663605-89-8) + [(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((R)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyl]-methanol (663606-08-4)

Guidance literature:

Multi-step reaction with 10 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

With 1H-imidazole; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; phosphate buffer; water; 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

Reference yield:

methyl (1S,2R,3S,5S)-3-hydroxy-5-isopropenyl-2-methylcyclopentanecarboxylate (663606-09-5) → [(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyl]-methanol (663605-89-8) + [(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((R)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyl]-methanol (663606-08-4)

Guidance literature:

Multi-step reaction with 8 steps

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

2: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C

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

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

5: sodium periodate / 20 °C

6: tetrahydrofuran / -78 °C

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

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

With 1H-imidazole; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; phosphate buffer; water; sodium hydride; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1002/anie.200353140

upstream raw materials:

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

C₂₈H₄₀O₃Si

(S)-carvone epoxide

(2R,3S,5S)-2-Chloro-5-isopropenyl-2-methyl-3-(tetrahydro-pyran-2-yloxy)-cyclohexanone

Downstream raw materials:

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

C₂₈H₄₀O₃Si

(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

(2aS,5aS,7S,7aS,9S,10R,10aR,10bS,10cR)-9-(tert-Butyl-diphenyl-silanyloxy)-7,10c-dihydroxy-2a,4,4,7,10-pentamethyl-decahydro-1,3,5-trioxa-benzo[cd]cyclopenta[h]azulen-2-one