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

Base Information

• Chemical Name: (1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentanecarbaldehyde
• CAS No.: 663606-11-9
• Molecular Formula: C₃₀H₄₂O₄Si
• Molecular Weight: 494.747
• Mol file: 663606-11-9.mol

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

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

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-cyclopentanecarbaldehyde

There total 18 articles about (1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentanecarbaldehyde 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: 90.0%

[(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-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentanecarbaldehyde (663606-11-9)

Guidance literature:

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; In dichloromethane; at 20 ℃;

DOI:10.1002/anie.200353140

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-cyclopentanecarbaldehyde (663606-11-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / phosphate buffer; dichloromethane / 0.5 h / 20 °C / pH 7

2: pyridine; Dess-Martin periodane / dichloromethane / 1 h / 20 °C

With pyridine; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In phosphate buffer; dichloromethane;

DOI:10.1002/chem.200700302

Reference yield:

(S)-carvone epoxide (672898-50-9) → (1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentanecarbaldehyde (663606-11-9)

Guidance literature:

Multi-step reaction with 13 steps

1: trifluoroacetic acid; lithium chloride / tetrahydrofuran / 20 °C

2: pyridinium p-toluenesulfonate / dichloromethane / 20 °C

3: sodium methylate / 0 °C

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

5: 1H-imidazole / N,N-dimethyl-formamide / 20 °C

6: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C

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

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

9: sodium periodate / 20 °C

10: tetrahydrofuran / -78 °C

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

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

13: N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve / dichloromethane / 20 °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; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; 3: Favorskii rearrangement;

DOI:10.1002/anie.200353140

upstream raw materials:

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

(S)-carvone epoxide

tert-butylchlorodiphenylsilane

(2R,3S,5S)-2-Chloro-3-hydroxy-5-isopropenyl-2-methyl-cyclohexanone

Downstream raw materials:

(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

C₂₈H₄₀O₃Si

C₂₈H₃₈O₃Si

trilobolide