<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

Base Information

• Chemical Name: <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
• CAS No.: 108712-57-8
• Molecular Formula: C₄₁H₆₆O₅Si₂
• Molecular Weight: 695.143

Synonyms:<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

Chemical Property of <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

Chemical Property:

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Technology Process of <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

There total 9 articles about <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 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: 61.0%

(3S,4S)-5-Benzenesulfonyl-4-[(1S,6S)-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-6-[(2S,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-3-methyl-hexanal → <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)

Guidance literature:

With disodium hydrogenphosphate; sodium amalgam; In methanol; for 1h; Ambient temperature;

DOI:10.1021/jo00392a009

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → <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)

Guidance literature:

Multi-step reaction with 7 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

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; tributylphosphine; methyllithium; dihydrogen peroxide; 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) → <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)

Guidance literature:

Multi-step reaction with 7 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

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; tributylphosphine; methyllithium; dihydrogen peroxide; 3-chloro-benzenecarboperoxoic acid; In methanol; diethyl ether; dichloromethane;

DOI:10.1021/jo00392a009

upstream raw materials:

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

2,2-Dimethyl-propionic acid (R)-2-[(1R,6R)-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-3-methyl-pent-4-enyl ester

Downstream raw materials:

(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

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