di-tert-butyl (1S,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(3,4-difluorophenyl)sulfanylmethyl]-4-hydroxy-bicyclo[3.1.0]-hexane-2,6-dicarboxylate

Base Information

Chemical Name:di-tert-butyl (1S,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(3,4-difluorophenyl)sulfanylmethyl]-4-hydroxy-bicyclo[3.1.0]-hexane-2,6-dicarboxylate
CAS No.:1377615-81-0
Molecular Formula:C₂₈H₃₉F₂NO₇S
Molecular Weight:571.683
Hs Code.:

di-tert-butyl (1S,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(3,4-difluorophenyl)sulfanylmethyl]-4-hydroxy-bicyclo[3.1.0]-hexane-2,6-dicarboxylate

Synonyms:di-tert-butyl (1S,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(3,4-difluorophenyl)sulfanylmethyl]-4-hydroxy-bicyclo[3.1.0]-hexane-2,6-dicarboxylate

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Chemical Property of di-tert-butyl (1S,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(3,4-difluorophenyl)sulfanylmethyl]-4-hydroxy-bicyclo[3.1.0]-hexane-2,6-dicarboxylate

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Technology Process of di-tert-butyl (1S,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(3,4-difluorophenyl)sulfanylmethyl]-4-hydroxy-bicyclo[3.1.0]-hexane-2,6-dicarboxylate

There total 4 articles about di-tert-butyl (1S,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(3,4-difluorophenyl)sulfanylmethyl]-4-hydroxy-bicyclo[3.1.0]-hexane-2,6-dicarboxylate 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: 89.0%

: 1377615-82-1
di-tert-butyl (1S,2R,3S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-{[(3,4-difluorophenyl)sulfanyl]methyl}-4-oxobicyclo[3.1.0]hexane-2,6-dicarboxylate

: 1377615-81-0
di-tert-butyl (1S,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(3,4-difluorophenyl)sulfanylmethyl]-4-hydroxy-bicyclo[3.1.0]-hexane-2,6-dicarboxylate

Guidance literature:: di-tert-butyl (1S,2R,3S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-{[(3,4-difluorophenyl)sulfanyl]methyl}-4-oxobicyclo[3.1.0]hexane-2,6-dicarboxylate; With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tert-butyl methyl ether; toluene; at -40 - 0 ℃; for 3h;

With methanol; In tert-butyl methyl ether; toluene; at 15 ℃; Product distribution / selectivity;

Reference yield:

: C₂₈H₃₇F₂NO₇S

: 1377615-81-0
di-tert-butyl (1S,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(3,4-difluorophenyl)sulfanylmethyl]-4-hydroxy-bicyclo[3.1.0]-hexane-2,6-dicarboxylate

Guidance literature:: With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; diethyl ether; at -10 - 20 ℃; for 1.16667h; stereoselective reaction;
DOI:10.1021/acs.jmedchem.6b01119

Reference yield:

: 635318-04-6
(1S,2S,5R,6R)-di-tert-butyl 2-[(tert-butoxycarbonyl)amino]-4-oxobicyclo[3.1.0]hexane-2,6-dicarboxylate

: 1377615-81-0
di-tert-butyl (1S,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(3,4-difluorophenyl)sulfanylmethyl]-4-hydroxy-bicyclo[3.1.0]-hexane-2,6-dicarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: toluene / 1 h / 80 °C

2: triethylamine; diisobutylaluminium hydride / toluene; tetrahydrofuran / 3 h / -78 °C

3: triethylamine / diethyl ether / 2 h / Heating

4: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; diethyl ether / 1.17 h / -10 - 20 °C

With dimethylsulfide borane complex; diisobutylaluminium hydride; triethylamine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; diethyl ether; toluene; 3: |Michael Addition;
DOI:10.1021/acs.jmedchem.6b01119