(3S,5R)-3-<(tert-butyldimethylsilyl)oxy>-1-ethynyl-5-hydroxy-2-methylcyclohex-1-ene

Base Information

• Chemical Name: (3S,5R)-3-<(tert-butyldimethylsilyl)oxy>-1-ethynyl-5-hydroxy-2-methylcyclohex-1-ene
• CAS No.: 122172-46-7
• Molecular Formula: C₁₅H₂₆O₂Si
• Molecular Weight: 266.456

Synonyms:(3S,5R)-3-<(tert-butyldimethylsilyl)oxy>-1-ethynyl-5-hydroxy-2-methylcyclohex-1-ene

Chemical Property of (3S,5R)-3-<(tert-butyldimethylsilyl)oxy>-1-ethynyl-5-hydroxy-2-methylcyclohex-1-ene

Chemical Property:

Purity/Quality:

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Technology Process of (3S,5R)-3-<(tert-butyldimethylsilyl)oxy>-1-ethynyl-5-hydroxy-2-methylcyclohex-1-ene

There total 13 articles about (3S,5R)-3-<(tert-butyldimethylsilyl)oxy>-1-ethynyl-5-hydroxy-2-methylcyclohex-1-ene 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: 100.0%

(3S,5R)-5-acetoxy-3-<(tert-butyldimethylsilyl)oxy>-1-ethynyl-2-methylcyclohex-1-ene (122172-37-6) → (3S,5R)-3-<(tert-butyldimethylsilyl)oxy>-1-ethynyl-5-hydroxy-2-methylcyclohex-1-ene (122172-46-7)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 2h;

DOI:10.1021/jo026474t

Reference yield: 100.0%

(3S,5R)-3-[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methyl-5-[(vinyloxy)carbonyloxy]cyclohex-1-ene → (3S,5R)-3-<(tert-butyldimethylsilyl)oxy>-1-ethynyl-5-hydroxy-2-methylcyclohex-1-ene (122172-46-7)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at 0 ℃; for 4h;

DOI:10.1016/j.bmc.2006.07.021

Reference yield: 23.0%

TB (116506-67-3) → (3S,5R)-5-<(tert-butyldimethylsilyl)oxy>-1-ethynyl-3-hydroxy-2-methylcyclohex-1-ene (122172-47-8) + (3S,5R)-3-<(tert-butyldimethylsilyl)oxy>-1-ethynyl-5-hydroxy-2-methylcyclohex-1-ene (122172-46-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.666667h; Ambient temperature;

DOI:10.1021/jo00278a018

upstream raw materials:

(3S,5R)-5-acetoxy-3-<(tert-butyldimethylsilyl)oxy>-1-ethynyl-2-methylcyclohex-1-ene

TB

(1S,5R)-5-acetoxy-1-ethynyl-3-hydroxy-2-methylcyclohex-1-ene

tert-butyldimethylsilyl chloride

Downstream raw materials:

(3S,5S)-3-[(tert-butyldimethylsilyl)oxy]-1-ehtynyl-5-hydroxy-2-methylcyclohex-1-ene

(3S,5R)-5-[(tert-butoxycarbonyl)amino]-3-[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene

(3S,5R)-3-[(tert-buthyldimethylsilyl)oxy]-1-ethynyl-2-methyl-5-phthalimidocyclohex-1-ene

3β-[(tert-butoxycarbonyl)amino]-3-deoxy-1α,25-dihydroprevitamin D₃

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