(2S,7S,8R,9S,12R)-4-Benzenesulfonyl-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-12-(tert-butyl-dimethyl-silanyloxymethyl)-2-((4S,6R)-2,2-di-tert-butyl-6-methyl-[1,3,2]dioxasilinan-4-yl)-8-methyl-tetradecan-5-one

Base Information

• Chemical Name: (2S,7S,8R,9S,12R)-4-Benzenesulfonyl-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-12-(tert-butyl-dimethyl-silanyloxymethyl)-2-((4S,6R)-2,2-di-tert-butyl-6-methyl-[1,3,2]dioxasilinan-4-yl)-8-methyl-tetradecan-5-one
• CAS No.: 189760-94-9
• Molecular Formula: C₅₂H₁₀₂O₈SSi₄
• Molecular Weight: 999.785

Synonyms:(2S,7S,8R,9S,12R)-4-Benzenesulfonyl-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-12-(tert-butyl-dimethyl-silanyloxymethyl)-2-((4S,6R)-2,2-di-tert-butyl-6-methyl-[1,3,2]dioxasilinan-4-yl)-8-methyl-tetradecan-5-one

Chemical Property of (2S,7S,8R,9S,12R)-4-Benzenesulfonyl-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-12-(tert-butyl-dimethyl-silanyloxymethyl)-2-((4S,6R)-2,2-di-tert-butyl-6-methyl-[1,3,2]dioxasilinan-4-yl)-8-methyl-tetradecan-5-one

Chemical Property:

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Useful:

Technology Process of (2S,7S,8R,9S,12R)-4-Benzenesulfonyl-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-12-(tert-butyl-dimethyl-silanyloxymethyl)-2-((4S,6R)-2,2-di-tert-butyl-6-methyl-[1,3,2]dioxasilinan-4-yl)-8-methyl-tetradecan-5-one

There total 21 articles about (2S,7S,8R,9S,12R)-4-Benzenesulfonyl-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-12-(tert-butyl-dimethyl-silanyloxymethyl)-2-((4S,6R)-2,2-di-tert-butyl-6-methyl-[1,3,2]dioxasilinan-4-yl)-8-methyl-tetradecan-5-one 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: 86.0%

(2S,7S,8R,9S,12R)-4-Benzenesulfonyl-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-12-(tert-butyl-dimethyl-silanyloxymethyl)-2-((4S,6R)-2,2-di-tert-butyl-6-methyl-[1,3,2]dioxasilinan-4-yl)-8-methyl-tetradecan-5-ol (189760-86-9) → (2S,7S,8R,9S,12R)-4-Benzenesulfonyl-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-12-(tert-butyl-dimethyl-silanyloxymethyl)-2-((4S,6R)-2,2-di-tert-butyl-6-methyl-[1,3,2]dioxasilinan-4-yl)-8-methyl-tetradecan-5-one (189760-94-9)

Guidance literature:

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(97)00585-6

Reference yield:

(2S,3S)-1-(benzyloxy)-2-methylhept-5-en-3-ol (106357-32-8) → (2S,7S,8R,9S,12R)-4-Benzenesulfonyl-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-12-(tert-butyl-dimethyl-silanyloxymethyl)-2-((4S,6R)-2,2-di-tert-butyl-6-methyl-[1,3,2]dioxasilinan-4-yl)-8-methyl-tetradecan-5-one (189760-94-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 90 percent / Et₃N / CH₂Cl₂ / 0 °C

2: 85 percent / O₂ / PdCl₂, CuCl / dimethylformamide; H₂O / Ambient temperature

3: 78 percent / HF, pyr / tetrahydrofuran / Ambient temperature

4: 82 percent / Me₄NBH(OAc)3 / acetonitrile; acetic acid / -30 °C

5: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

6: 96 percent / H₂ / 3 percent Pt/C / ethanol

7: 96 percent / I₂, Ph₃P, imidazole / benzene / Heating

8: 85 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 °C / to RT

9: 86 percent / n-BuLi, BF₃*Et₂O / tetrahydrofuran / -78 °C / to RT

10: 86 percent / TPAP, NMO, 4 Angstroem molecular sieve / CH₂Cl₂ / Ambient temperature

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen fluoride; hydrogen; iodine; oxygen; triethylamine; triphenylphosphine; tetramethylammonium triacetoxyborohydride; platinum on activated charcoal; copper(l) chloride; palladium dichloride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1016/S0040-4039(97)00585-6

Reference yield:

(4S,5S)-5-benzyloxymethyl-4-hydroxyhexan-2-one (189760-73-4) → (2S,7S,8R,9S,12R)-4-Benzenesulfonyl-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-12-(tert-butyl-dimethyl-silanyloxymethyl)-2-((4S,6R)-2,2-di-tert-butyl-6-methyl-[1,3,2]dioxasilinan-4-yl)-8-methyl-tetradecan-5-one (189760-94-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 82 percent / Me₄NBH(OAc)3 / acetonitrile; acetic acid / -30 °C

2: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

3: 96 percent / H₂ / 3 percent Pt/C / ethanol

4: 96 percent / I₂, Ph₃P, imidazole / benzene / Heating

5: 85 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 °C / to RT

6: 86 percent / n-BuLi, BF₃*Et₂O / tetrahydrofuran / -78 °C / to RT

7: 86 percent / TPAP, NMO, 4 Angstroem molecular sieve / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; 2,6-dimethylpyridine; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; iodine; triphenylphosphine; tetramethylammonium triacetoxyborohydride; platinum on activated charcoal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; acetic acid; acetonitrile; benzene;

DOI:10.1016/S0040-4039(97)00585-6

upstream raw materials:

(2S,7S,8R,9S,12R)-4-Benzenesulfonyl-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-12-(tert-butyl-dimethyl-silanyloxymethyl)-2-((4S,6R)-2,2-di-tert-butyl-6-methyl-[1,3,2]dioxasilinan-4-yl)-8-methyl-tetradecan-5-ol

methylphenylsulfonate

t-butyldimethylsiyl triflate

(2S,3S)-1-(benzyloxy)-2-methylhept-5-en-3-ol

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