(3S,4S)-4-[(1S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-6-[(2R,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-3-methyl-hexanal

Base Information

• Chemical Name: (3S,4S)-4-[(1S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-6-[(2R,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-3-methyl-hexanal
• CAS No.: 108712-58-9
• Molecular Formula: C₄₁H₆₄O₅Si₂
• Molecular Weight: 693.127

Synonyms:

Chemical Property of (3S,4S)-4-[(1S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-6-[(2R,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-3-methyl-hexanal

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of (3S,4S)-4-[(1S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-6-[(2R,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-3-methyl-hexanal

There total 10 articles about (3S,4S)-4-[(1S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-6-[(2R,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-3-methyl-hexanal 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:

<2R-<2α<γS*,?S*(1S*,6S*)>,4β,6α>>-?-<6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-cyclohexen-1-yl>-4-<<(1,1-dimethylethyl)diphenylsilyl>oxy>tetrahydro-6-methoxy-γ-(S)-methyl-2H-pyran-2-hexanol (108712-57-8) → (3S,4S)-4-[(1S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-6-[(2R,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-3-methyl-hexanal (108712-58-9)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; for 0.5h;

DOI:10.1021/jo00392a009

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (3S,4S)-4-[(1S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-6-[(2R,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-3-methyl-hexanal (108712-58-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / Ambient temperature

2: 78 percent / methyllithium / diethyl ether / 0.5 h / 0 °C

3: 1.) tri-n-butylphosphine / 1.) benzene, 5 min, 2.) benzene, RT, 2 h

4: 95 percent / m-chloroperoxybenzoic acid / diethyl ether / 0.08 h / 0 °C

5: 1.) hexamethylphosphoramide, n-butyllithium / 1.) THF, hexane, 30 min, 2.) THF, hexane, RT, 6 h

6: 1.) 9-borabicyclo<3,3,1>nonane, 2.) 3 N aq. sodium hydroxide, 30percent aq. H₂O₂ / 1.) THF, RT, 2 h, 2.) THF, 50 deg C, 30 min

7: 61 percent / disodium hydrogen phosphate, sodium amalgam / methanol / 1 h / Ambient temperature

8: oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; disodium hydrogenphosphate; sodium amalgam; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; tributylphosphine; methyllithium; dihydrogen peroxide; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; In methanol; diethyl ether; dichloromethane;

DOI:10.1021/jo00392a009

Reference yield:

2,2-Dimethyl-propionic acid (R)-2-((1R,6R)-6-hydroxy-cyclohex-2-enyl)-3-methyl-pent-4-enyl ester (108712-50-1) → (3S,4S)-4-[(1S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-6-[(2R,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-3-methyl-hexanal (108712-58-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / Ambient temperature

2: 78 percent / methyllithium / diethyl ether / 0.5 h / 0 °C

3: 1.) tri-n-butylphosphine / 1.) benzene, 5 min, 2.) benzene, RT, 2 h

4: 95 percent / m-chloroperoxybenzoic acid / diethyl ether / 0.08 h / 0 °C

5: 1.) hexamethylphosphoramide, n-butyllithium / 1.) THF, hexane, 30 min, 2.) THF, hexane, RT, 6 h

6: 1.) 9-borabicyclo<3,3,1>nonane, 2.) 3 N aq. sodium hydroxide, 30percent aq. H₂O₂ / 1.) THF, RT, 2 h, 2.) THF, 50 deg C, 30 min

7: 61 percent / disodium hydrogen phosphate, sodium amalgam / methanol / 1 h / Ambient temperature

8: oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; disodium hydrogenphosphate; sodium amalgam; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; tributylphosphine; methyllithium; dihydrogen peroxide; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; In methanol; diethyl ether; dichloromethane;

DOI:10.1021/jo00392a009

upstream raw materials:

<2R-<2α<γS^*,?S^*(1S^*,6S^*)>,4β,6α>>-?-<6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-cyclohexen-1-yl>-4-<<(1,1-dimethylethyl)diphenylsilyl>oxy>tetrahydro-6-methoxy-γ-(S)-methyl-2H-pyran-2-hexanol

t-butyldimethylsiyl triflate

2,2-Dimethyl-propionic acid (R)-2-((1R,6R)-6-hydroxy-cyclohex-2-enyl)-3-methyl-pent-4-enyl ester

<1α,2α(1R^*,2R^*)>-(+/-)-(1,1-dimethylethyl)dimethyl<<2-<2-methyl-1-<(phenylthio)methyl>-3-butenyl>-3-cyclohexen-1-yl>oxy>silane

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