3α,4α-dihydroxy-1β-((benzoyloxy)methyl)-1-(1-methyl-4-hydroxy-4-methylcyclohex-2-enyl)-2β-((tert-butyldimethylsilyl)oxy)cyclopentane

Base Information

• Chemical Name: 3α,4α-dihydroxy-1β-((benzoyloxy)methyl)-1-(1-methyl-4-hydroxy-4-methylcyclohex-2-enyl)-2β-((tert-butyldimethylsilyl)oxy)cyclopentane
• CAS No.: 101933-65-7
• Molecular Formula: C₂₇H₄₂O₆Si
• Molecular Weight: 490.712
• Mol file: 101933-65-7.mol

Synonyms:

Chemical Property of 3α,4α-dihydroxy-1β-((benzoyloxy)methyl)-1-(1-methyl-4-hydroxy-4-methylcyclohex-2-enyl)-2β-((tert-butyldimethylsilyl)oxy)cyclopentane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3α,4α-dihydroxy-1β-((benzoyloxy)methyl)-1-(1-methyl-4-hydroxy-4-methylcyclohex-2-enyl)-2β-((tert-butyldimethylsilyl)oxy)cyclopentane

There total 3 articles about 3α,4α-dihydroxy-1β-((benzoyloxy)methyl)-1-(1-methyl-4-hydroxy-4-methylcyclohex-2-enyl)-2β-((tert-butyldimethylsilyl)oxy)cyclopentane 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:

3α,4α-diacetoxy-1β-((benzoyloxy)methyl)-1-(1-methyl-4-hydroxy-4-methylcyclohex-2-enyl)-2β-((tert-butyldimethylsilyl)oxy)cyclopentane (101933-64-6) → 3α,4α-dihydroxy-1β-((benzoyloxy)methyl)-1-(1-methyl-4-hydroxy-4-methylcyclohex-2-enyl)-2β-((tert-butyldimethylsilyl)oxy)cyclopentane (101933-65-7)

Guidance literature:

With potassium carbonate; In methanol; water; for 2h; Ambient temperature;

DOI:10.1021/jo00361a001

Reference yield:

3α,4α-diacetoxy-1β-((benzoyloxy)methyl)-1-(1-methyl-4-oxocyclohex-2-enyl)-2β-((tert-butyldimethylsilyl)oxy)cyclopentane (101933-52-2) → 3α,4α-dihydroxy-1β-((benzoyloxy)methyl)-1-(1-methyl-4-hydroxy-4-methylcyclohex-2-enyl)-2β-((tert-butyldimethylsilyl)oxy)cyclopentane (101933-65-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 919 mg / diethyl ether; tetrahydrofuran / 2.5 h / -78 °C

2: 728 mg / potassium carbonate / methanol; H₂O / 2 h / Ambient temperature

With potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; water;

DOI:10.1021/jo00361a001

Reference yield:

3α,4α-diacetoxy-1β-((benzoyloxy)methyl)-1-(4-methoxy-1-methylcyclohexa-2,4-dienyl)-2β-((tert-butyldimethylsilyl)oxy)cyclopentane → 3α,4α-dihydroxy-1β-((benzoyloxy)methyl)-1-(1-methyl-4-hydroxy-4-methylcyclohex-2-enyl)-2β-((tert-butyldimethylsilyl)oxy)cyclopentane (101933-65-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / oxalic acid / methanol; H₂O / 1 h / Ambient temperature

2: 919 mg / diethyl ether; tetrahydrofuran / 2.5 h / -78 °C

3: 728 mg / potassium carbonate / methanol; H₂O / 2 h / Ambient temperature

With oxalic acid; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; water;

DOI:10.1021/jo00361a001

upstream raw materials:

3α,4α-diacetoxy-1β-((benzoyloxy)methyl)-1-(1-methyl-4-hydroxy-4-methylcyclohex-2-enyl)-2β-((tert-butyldimethylsilyl)oxy)cyclopentane

3α,4α-diacetoxy-1β-((benzoyloxy)methyl)-1-(1-methyl-4-oxocyclohex-2-enyl)-2β-((tert-butyldimethylsilyl)oxy)cyclopentane

Downstream raw materials:

3α-acetoxy-14-(benzoyloxy)-12β-((tert-butyldimethylsilyl)oxy)-13-nortrichothec-9-ene

3α-acetoxy-14-(benzoyloxy)-13-nortrichothec-9-en-12-one

3α-acetoxy-14-(benzoyloxy)-12β-hydroxy-13-nortrichothec-9-ene

14-(benzyloxy)-12β-((tert-butyldimethylsilyl)oxy)-3α-hydroxy-13-nortrichothec-9-ene