(5E)-23-phenylsulfonyl-1α,25-dihydroxyvitamin D₃ 1,3-di-tert-butyldiphenylsilyl-25-methoxymethyl ether

Base Information

• Chemical Name: (5E)-23-phenylsulfonyl-1α,25-dihydroxyvitamin D₃ 1,3-di-tert-butyldiphenylsilyl-25-methoxymethyl ether
• CAS No.: 336128-28-0
• Molecular Formula: C₆₇H₈₈O₆SSi₂
• Molecular Weight: 1077.67

Synonyms:(5E)-23-phenylsulfonyl-1α,25-dihydroxyvitamin D₃ 1,3-di-tert-butyldiphenylsilyl-25-methoxymethyl ether

Chemical Property of (5E)-23-phenylsulfonyl-1α,25-dihydroxyvitamin D₃ 1,3-di-tert-butyldiphenylsilyl-25-methoxymethyl ether

Chemical Property:

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Technology Process of (5E)-23-phenylsulfonyl-1α,25-dihydroxyvitamin D₃ 1,3-di-tert-butyldiphenylsilyl-25-methoxymethyl ether

There total 2 articles about (5E)-23-phenylsulfonyl-1α,25-dihydroxyvitamin D₃ 1,3-di-tert-butyldiphenylsilyl-25-methoxymethyl ether 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: 83.0%

(3-Methoxymethoxy-3-methyl-butane-1-sulfonyl)-benzene (214351-87-8) + (1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-diphenyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-1-((S)-2-iodo-1-methyl-ethyl)-7a-methyl-octahydro-indene (162636-76-2) → (5E)-23-phenylsulfonyl-1α,25-dihydroxyvitamin D3 1,3-di-tert-butyldiphenylsilyl-25-methoxymethyl ether (336128-28-0)

Guidance literature:

(3-Methoxymethoxy-3-methyl-butane-1-sulfonyl)-benzene; With lithium diisopropyl amide; In tetrahydrofuran; at -20 ℃; for 0.333333h;

(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-diphenyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-1-((S)-2-iodo-1-methyl-ethyl)-7a-methyl-octahydro-indene; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; at -20 ℃; for 2h;

DOI:10.1248/cpb.49.312

Reference yield:

22-iodo-23,24,25,26,27-pentanor-1α-hydroxyvitamin D3 1,3-di-tert-butyldiphenylsilyl ether-SO2 adduct → (5E)-23-phenylsulfonyl-1α,25-dihydroxyvitamin D3 1,3-di-tert-butyldiphenylsilyl-25-methoxymethyl ether (336128-28-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 92 percent / NaHCO₃ / ethanol / 3 h / Heating

2.1: LDA / tetrahydrofuran / 0.33 h / -20 °C

2.2: 83 percent / HMPA / tetrahydrofuran / 2 h / -20 °C

With sodium hydrogencarbonate; lithium diisopropyl amide; In tetrahydrofuran; ethanol;

DOI:10.1248/cpb.49.312

Reference yield: 65.0%

(5E)-23-phenylsulfonyl-1α,25-dihydroxyvitamin D3 1,3-di-tert-butyldiphenylsilyl-25-methoxymethyl ether (336128-28-0) → (5E)-1α,25-dihydroxyvitamin D3 1,3-di-tert-butyldiphenylsilyl-25-methoxymethyl ether (336128-29-1)

Guidance literature:

With methanol; sodium amalgam; In tetrahydrofuran; at 0 ℃;

DOI:10.1248/cpb.49.312

upstream raw materials:

(3-Methoxymethoxy-3-methyl-butane-1-sulfonyl)-benzene

(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-diphenyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-1-((S)-2-iodo-1-methyl-ethyl)-7a-methyl-octahydro-indene

Downstream raw materials:

(5E)-1α,25-dihydroxyvitamin D₃ 1,3-di-tert-butyldiphenylsilyl-25-methoxymethyl ether

10-oxo-19-nor-1α,25-dihydroxyvitamin D₃ 1,3-di-tert-butyldiphenylsilyl-25-methoxymethyl ether

(6S,8R)-6,8-Bis-(tert-butyl-diphenyl-silanyloxy)-10-[2-[(1R,3aS,7aR)-1-((R)-5-methoxymethoxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-3-methyl-1-oxa-2-aza-spiro[4.5]dec-2-ene

(2S,4R)-1-(Benzenesulfonyl-fluoro-methyl)-2,4-bis-(tert-butyl-diphenyl-silanyloxy)-6-[2-[(1R,3aS,7aR)-1-((R)-5-methoxymethoxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-cyclohexanol

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