(2R)-1-benzoyloxy-2-hydroxy-6-(t-butyldimethylsilyloxy)-hexan-4-one ethylene dithioacetal

Base Information

• Chemical Name: (2R)-1-benzoyloxy-2-hydroxy-6-(t-butyldimethylsilyloxy)-hexan-4-one ethylene dithioacetal
• CAS No.: 83181-95-7
• Molecular Formula: C₂₁H₃₄O₄S₂Si
• Molecular Weight: 442.716
• Mol file: 83181-95-7.mol

Synonyms:(2R)-1-benzoyloxy-2-hydroxy-6-(t-butyldimethylsilyloxy)-hexan-4-one ethylene dithioacetal

Chemical Property of (2R)-1-benzoyloxy-2-hydroxy-6-(t-butyldimethylsilyloxy)-hexan-4-one ethylene dithioacetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-1-benzoyloxy-2-hydroxy-6-(t-butyldimethylsilyloxy)-hexan-4-one ethylene dithioacetal

There total 5 articles about (2R)-1-benzoyloxy-2-hydroxy-6-(t-butyldimethylsilyloxy)-hexan-4-one ethylene dithioacetal 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: 88.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (2R)-1-benzoyloxy-2,6-dihydroxyhexan-4-one ethylene dithioacetal (77003-58-8) → (2R)-1-benzoyloxy-2-hydroxy-6-(t-butyldimethylsilyloxy)-hexan-4-one ethylene dithioacetal (83181-95-7)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 10h;

Reference yield:

(7R,8R,9R)-9-benzoyloxy-7,8-dihydroxy-1,4-dithiaspiro<4.5>decane (77003-55-5,77058-19-6) → (2R)-1-benzoyloxy-2-hydroxy-6-(t-butyldimethylsilyloxy)-hexan-4-one ethylene dithioacetal (83181-95-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Ph₃BiCO₃, 2.) NaBH₄ / 1.) CH₂Cl₂, reflux, 6 h, 2.) EtOH, H₂O, 1 h

2: tetramethylguanidine / CH₂Cl₂ / 2 h

3: 88 percent / Et₃N, DMAP / CH₂Cl₂ / 10 h

With dmap; sodium tetrahydroborate; 1,1,3,3-tetramethylguanidine; Ph₃BiCO₃; triethylamine; In dichloromethane;

Reference yield:

(3R,4R,5R)-3-benzoyloxy-4,5-dihydroxycyclohexanone 4,5-O-cyclohexylidene acetal (77003-54-4) → (2R)-1-benzoyloxy-2-hydroxy-6-(t-butyldimethylsilyloxy)-hexan-4-one ethylene dithioacetal (83181-95-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / ZnI₂ / CH₂Cl₂

2: 1.) Ph₃BiCO₃, 2.) NaBH₄ / 1.) CH₂Cl₂, reflux, 6 h, 2.) EtOH, H₂O, 1 h

3: 88 percent / Et₃N, DMAP / CH₂Cl₂ / 10 h

With dmap; sodium tetrahydroborate; Ph₃BiCO₃; triethylamine; zinc(II) iodide; In dichloromethane;

upstream raw materials:

tert-butyldimethylsilyl chloride

(2R)-1-benzoyloxy-2,6-dihydroxyhexan-4-one ethylene dithioacetal

(7R,8R,9R)-9-benzoyloxy-7,8-dihydroxy-1,4-dithiaspiro<4.5>decane

(3R,4R,5R)-3-benzoyloxy-4,5-dihydroxycyclohexanone 4,5-O-cyclohexylidene acetal

Downstream raw materials:

(2R)-1-benzoyloxy-2-methanesulfonyloxy-6-(t-butyldimethylsiloxy)hexan-4-one ethylene dithioacetal

(2R)-1-benzoyloxy-6-hydroxy-2-methanesulfonyloxyhexan-4-one ethylene dithioacetal

(2R)-1-benzoyloxy-5-formyl-2-methylsulphonyloxypentan-4-one ethylene dithioacetal

(2R)-1-benzoyloxy-5-(5,5-dimethyl-1,3-dioxan-2-yl)-2-methanesulphonyloxypentan-4-one ethylene dithioacetal