2,6:5,9:8,12-Trianhydro-10-O-benzyl-10-O-(tert-butyldiphenylsilyl)-4,7,11-trideoxy-9-C-methyl-1-aldehyde-D-threo-L-allo-L-glycero-3-trideculose diethyl mercaptole

Base Information

Chemical Name:2,6:5,9:8,12-Trianhydro-10-O-benzyl-10-O-(tert-butyldiphenylsilyl)-4,7,11-trideoxy-9-C-methyl-1-aldehyde-D-threo-L-allo-L-glycero-3-trideculose diethyl mercaptole
CAS No.:122821-77-6
Molecular Formula:C₄₁H₅₄O₆S₂Si
Molecular Weight:735.094
Hs Code.:

2,6:5,9:8,12-Trianhydro-10-O-benzyl-10-O-(tert-butyldiphenylsilyl)-4,7,11-trideoxy-9-C-methyl-1-aldehyde-D-threo-L-allo-L-glycero-3-trideculose diethyl mercaptole

Synonyms:2,6:5,9:8,12-Trianhydro-10-O-benzyl-10-O-(tert-butyldiphenylsilyl)-4,7,11-trideoxy-9-C-methyl-1-aldehyde-D-threo-L-allo-L-glycero-3-trideculose diethyl mercaptole

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Chemical Property of 2,6:5,9:8,12-Trianhydro-10-O-benzyl-10-O-(tert-butyldiphenylsilyl)-4,7,11-trideoxy-9-C-methyl-1-aldehyde-D-threo-L-allo-L-glycero-3-trideculose diethyl mercaptole

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Technology Process of 2,6:5,9:8,12-Trianhydro-10-O-benzyl-10-O-(tert-butyldiphenylsilyl)-4,7,11-trideoxy-9-C-methyl-1-aldehyde-D-threo-L-allo-L-glycero-3-trideculose diethyl mercaptole

There total 7 articles about 2,6:5,9:8,12-Trianhydro-10-O-benzyl-10-O-(tert-butyldiphenylsilyl)-4,7,11-trideoxy-9-C-methyl-1-aldehyde-D-threo-L-allo-L-glycero-3-trideculose diethyl mercaptole 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: 83.0%

: 122844-54-6
2,6:5,9:8,12-Trianhydro-10-O-benzyl-10-O-(tert-butyldiphenylsilyl)-4,7,11-trideoxy-9-C-methyl-D-threo-L-allo-L-glycero-3-trideculose diethyl mercaptole

: 122821-77-6
2,6:5,9:8,12-Trianhydro-10-O-benzyl-10-O-(tert-butyldiphenylsilyl)-4,7,11-trideoxy-9-C-methyl-1-aldehyde-D-threo-L-allo-L-glycero-3-trideculose diethyl mercaptole

Guidance literature:: With pyridine-SO₃ complex; triethylamine; In dichloromethane; dimethyl sulfoxide; at 0 ℃; for 1.5h;
DOI:10.1021/ja00199a031

Reference yield:

: 122822-08-6
2,6:5,9:8,12-Trianhydro-4-O-benzyl-1-O-(tert-butyldiphenylsilyl)-3,7,10-trideoxy-5-C-methyl-D-allo-D-altro-tridecitol

: 122821-77-6
2,6:5,9:8,12-Trianhydro-10-O-benzyl-10-O-(tert-butyldiphenylsilyl)-4,7,11-trideoxy-9-C-methyl-1-aldehyde-D-threo-L-allo-L-glycero-3-trideculose diethyl mercaptole

Guidance literature:: Multi-step reaction with 4 steps

1: 91 percent / imidazole / dimethylformamide / 0.5 h / 0 °C

2: 1.) oxalyl chloride, DMSO, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) 0 deg C, 10 min

3: 1.) zinc triflate (Zn(OTf)2), 2.) CSA / 1.) CH₂Cl₂, 30 min, 2.) MeOH, 15 min

4: 83 percent / triethylamine, SO₃*pyr / CH₂Cl₂; dimethylsulfoxide / 1.5 h / 0 °C

With 1H-imidazole; oxalyl dichloride; pyridine-SO₃ complex; camphor-10-sulfonic acid; zinc trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/ja00199a031

Reference yield:

: 122822-04-2
Methy (E)-4,8:7,11:10,14-trianhydro-12-O-benzyl-15-O-(tert-butyldiphenylsilyl)-2,3,6,9,13-pentadeoxy-11-C-methyl-D-talo-L-allo-pentadec-2-enonate

: 122821-77-6
2,6:5,9:8,12-Trianhydro-10-O-benzyl-10-O-(tert-butyldiphenylsilyl)-4,7,11-trideoxy-9-C-methyl-1-aldehyde-D-threo-L-allo-L-glycero-3-trideculose diethyl mercaptole

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) ozone, 2.) Me₂S, Ph₃P, NaBH₄ / 1.) CH₂Cl₂, -78 deg C, 2.) MeOH, r.t., 1 h

2: 91 percent / imidazole / dimethylformamide / 0.5 h / 0 °C

3: 1.) oxalyl chloride, DMSO, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) 0 deg C, 10 min

4: 1.) zinc triflate (Zn(OTf)2), 2.) CSA / 1.) CH₂Cl₂, 30 min, 2.) MeOH, 15 min

5: 83 percent / triethylamine, SO₃*pyr / CH₂Cl₂; dimethylsulfoxide / 1.5 h / 0 °C

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; pyridine-SO₃ complex; dimethylsulfide; camphor-10-sulfonic acid; zinc trifluoromethanesulfonate; ozone; dimethyl sulfoxide; triethylamine; triphenylphosphine; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/ja00199a031