(2R,3R,4R,5S,6R)-3,5-(di-tert-butylsilylenedioxy)-4-ethyl-2,6-dimethyl-1-(2',2'-dimethylpropanoyloxy)-7-(para-tolylsulfonyloxy)heptane

Base Information

Chemical Name:(2R,3R,4R,5S,6R)-3,5-(di-tert-butylsilylenedioxy)-4-ethyl-2,6-dimethyl-1-(2',2'-dimethylpropanoyloxy)-7-(para-tolylsulfonyloxy)heptane
CAS No.:192993-21-8
Molecular Formula:C₃₁H₅₄O₇SSi
Molecular Weight:598.917
Hs Code.:

Synonyms:(2R,3R,4R,5S,6R)-3,5-(di-tert-butylsilylenedioxy)-4-ethyl-2,6-dimethyl-1-(2',2'-dimethylpropanoyloxy)-7-(para-tolylsulfonyloxy)heptane

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Chemical Property of (2R,3R,4R,5S,6R)-3,5-(di-tert-butylsilylenedioxy)-4-ethyl-2,6-dimethyl-1-(2',2'-dimethylpropanoyloxy)-7-(para-tolylsulfonyloxy)heptane

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Technology Process of (2R,3R,4R,5S,6R)-3,5-(di-tert-butylsilylenedioxy)-4-ethyl-2,6-dimethyl-1-(2',2'-dimethylpropanoyloxy)-7-(para-tolylsulfonyloxy)heptane

There total 12 articles about (2R,3R,4R,5S,6R)-3,5-(di-tert-butylsilylenedioxy)-4-ethyl-2,6-dimethyl-1-(2',2'-dimethylpropanoyloxy)-7-(para-tolylsulfonyloxy)heptane 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: 99.0%

: 1352831-90-3
(2R,3S,4S,5R,6R)-3,5-(di-tert-butylsilylenedioxy)-4-ethyl-2,6-dimethyl-7-(2',2'-dimethylpropanoyloxy)heptan-1-ol

: 98-59-9
p-toluenesulfonyl chloride

: 192993-21-8
(2R,3R,4R,5S,6R)-3,5-(di-tert-butylsilylenedioxy)-4-ethyl-2,6-dimethyl-1-(2',2'-dimethylpropanoyloxy)-7-(para-tolylsulfonyloxy)heptane

Guidance literature:: With pyridine; at 20 ℃; for 16h; Inert atmosphere;
DOI:10.1016/j.tet.2011.09.012

Reference yield:

: 192993-13-8
(2R)-1-benzyloxy-2-methylhexan-3-one

: 192993-21-8
(2R,3R,4R,5S,6R)-3,5-(di-tert-butylsilylenedioxy)-4-ethyl-2,6-dimethyl-1-(2',2'-dimethylpropanoyloxy)-7-(para-tolylsulfonyloxy)heptane

Guidance literature:: Multi-step reaction with 6 steps

1: Et₃N / diethyl ether / 2 h / 0 °C

2: 2.) Et₃N, LiBH₄ / 1.) -20 deg C, 1.5 h; 2.) -78 deg C, 1.5 h

3: H₂O₂, NaOH / methanol / 1 h / 0 - 20 °C

4: 2,6-lutidine / CH₂Cl₂ / 2.5 h / 0 - 20 °C

5: 1.) 9-BBN; 2.) H₂O₂, NaOH / 1.) THF, 0-20 deg C, 3 h; 2.) MeOH, 1 h

6: 1.) 10percent Pd/C, H₂; 2.) py / 1.) THF, 3 h; 2.) 16 h

With pyridine; 2,6-dimethylpyridine; sodium hydroxide; palladium on activated charcoal; lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; hydrogen; dihydrogen peroxide; triethylamine; In methanol; diethyl ether; dichloromethane;
DOI:10.1016/S0040-4039(97)00816-2

Reference yield:

: 192993-18-3
(3S,4S,5S,6R)-7-benzyloxy-4-ethyl-2,6-dimethylhept-1-ene-3,5-diol

: 192993-21-8
(2R,3R,4R,5S,6R)-3,5-(di-tert-butylsilylenedioxy)-4-ethyl-2,6-dimethyl-1-(2',2'-dimethylpropanoyloxy)-7-(para-tolylsulfonyloxy)heptane

Guidance literature:: Multi-step reaction with 3 steps

1: 2,6-lutidine / CH₂Cl₂ / 2.5 h / 0 - 20 °C

2: 1.) 9-BBN; 2.) H₂O₂, NaOH / 1.) THF, 0-20 deg C, 3 h; 2.) MeOH, 1 h

3: 1.) 10percent Pd/C, H₂; 2.) py / 1.) THF, 3 h; 2.) 16 h

With pyridine; 2,6-dimethylpyridine; sodium hydroxide; palladium on activated charcoal; 9-borabicyclo[3.3.1]nonane dimer; hydrogen; dihydrogen peroxide; In dichloromethane;
DOI:10.1016/S0040-4039(97)00816-2