[3S,4S,5R,6S]-4,5-di-O-benzyl-3-O-tert-butyl(dimethyl)silyl-3,4,5,6-tetrahydroxycycloheptan-1-one 1,3-propanedithioketal

Base Information

• Chemical Name: [3S,4S,5R,6S]-4,5-di-O-benzyl-3-O-tert-butyl(dimethyl)silyl-3,4,5,6-tetrahydroxycycloheptan-1-one 1,3-propanedithioketal
• CAS No.: 243978-85-0
• Molecular Formula: C₃₀H₄₄O₄S₂Si
• Molecular Weight: 560.894
• Mol file: 243978-85-0.mol

Synonyms:[3S,4S,5R,6S]-4,5-di-O-benzyl-3-O-tert-butyl(dimethyl)silyl-3,4,5,6-tetrahydroxycycloheptan-1-one 1,3-propanedithioketal

Chemical Property of [3S,4S,5R,6S]-4,5-di-O-benzyl-3-O-tert-butyl(dimethyl)silyl-3,4,5,6-tetrahydroxycycloheptan-1-one 1,3-propanedithioketal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [3S,4S,5R,6S]-4,5-di-O-benzyl-3-O-tert-butyl(dimethyl)silyl-3,4,5,6-tetrahydroxycycloheptan-1-one 1,3-propanedithioketal

There total 1 articles about [3S,4S,5R,6S]-4,5-di-O-benzyl-3-O-tert-butyl(dimethyl)silyl-3,4,5,6-tetrahydroxycycloheptan-1-one 1,3-propanedithioketal 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: 63.0%

tert-butyl(1,3-dithian-2-yl)dimethylsilane (95452-06-5) + 1,2:5,6-dianhydro-3,4-di-O-benzyl-L-iditol (157363-84-3) → [3S,4S,5R,6R]-4,5-di-O-benzyl-3-O-tert-butyl(dimethyl)silyl-6-hydroxymethyl-3,4,5-trihydroxycyclohexan-1-one 1,3-propanedithioketal + [3S,4S,5R,6S]-4,5-di-O-benzyl-3-O-tert-butyl(dimethyl)silyl-3,4,5,6-tetrahydroxycycloheptan-1-one 1,3-propanedithioketal (243978-85-0)

Guidance literature:

tert-butyl(1,3-dithian-2-yl)dimethylsilane; With n-butyllithium; dibutylmagnesium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;

1,2:5,6-dianhydro-3,4-di-O-benzyl-L-iditol; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at 20 ℃;

Reference yield: 100.0%

tert-butyldimethylsilyl chloride (18162-48-6) + [3S,4S,5R,6S]-4,5-di-O-benzyl-3-O-tert-butyl(dimethyl)silyl-3,4,5,6-tetrahydroxycycloheptan-1-one 1,3-propanedithioketal (243978-85-0) → [3S,4S,5S,6S]-4,5-dibenzyloxy-3,6-di-tert-butyl(dimethyl)silyloxycycloheptan-1-one 1,3-propanedithioketal (243978-56-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 70 ℃; for 24h;

DOI:10.1016/j.tet.2003.09.049

Reference yield:

[3S,4S,5R,6S]-4,5-di-O-benzyl-3-O-tert-butyl(dimethyl)silyl-3,4,5,6-tetrahydroxycycloheptan-1-one 1,3-propanedithioketal (243978-85-0) → [3S,4S,5S,6S]-4,5-dibenzyloxy-3,6-di-tert-butyl(dimethyl)silyloxycycloheptan-1-one (243978-64-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / imidazole / dimethylformamide / 24 h / 70 °C

2: 79 percent / N-bromosuccinimide / acetone; H₂O / 0.5 h / -25 °C

With 1H-imidazole; N-Bromosuccinimide; In water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.tet.2003.09.049

upstream raw materials:

tert-butyl(1,3-dithian-2-yl)dimethylsilane

1,2:5,6-dianhydro-3,4-di-O-benzyl-L-iditol

Downstream raw materials:

[3S,4S,5S,6S]-4,5-dibenzyloxy-3,6-di-tert-butyl(dimethyl)silyloxycycloheptan-1-one 1,3-propanedithioketal

[3S,4S,5S,6S]-4,5-dibenzyloxy-3,6-di-tert-butyl(dimethyl)silyloxycycloheptan-1-one

[3S,4S,5S,6S]-N-[4,5-dibenzyloxy-3,6-di-tert-butyl(dimethyl)silyloxycycloheptanyl]-N-benzylamine

N-([3S,4R,5R,6S]-4,5-di-O-benzyl-3,4,5,6-tetrahydroxycycloheptanyl)-N-butylamine