tert-butyl (3aR,4S,7R,7aS)-2,2-dimethyl-5-[(4-methylphenyl)sulfonyl]-3a,4,7,7a-tetrahydro-4,7-epimino-1,3-benzodioxole-8-carboxylate

Base Information

Chemical Name:tert-butyl (3aR,4S,7R,7aS)-2,2-dimethyl-5-[(4-methylphenyl)sulfonyl]-3a,4,7,7a-tetrahydro-4,7-epimino-1,3-benzodioxole-8-carboxylate
CAS No.:205813-79-2
Molecular Formula:C₂₁H₂₇NO₆S
Molecular Weight:421.514
Hs Code.:

Synonyms:tert-butyl (3aR,4S,7R,7aS)-2,2-dimethyl-5-[(4-methylphenyl)sulfonyl]-3a,4,7,7a-tetrahydro-4,7-epimino-1,3-benzodioxole-8-carboxylate

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Chemical Property of tert-butyl (3aR,4S,7R,7aS)-2,2-dimethyl-5-[(4-methylphenyl)sulfonyl]-3a,4,7,7a-tetrahydro-4,7-epimino-1,3-benzodioxole-8-carboxylate

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Technology Process of tert-butyl (3aR,4S,7R,7aS)-2,2-dimethyl-5-[(4-methylphenyl)sulfonyl]-3a,4,7,7a-tetrahydro-4,7-epimino-1,3-benzodioxole-8-carboxylate

There total 14 articles about tert-butyl (3aR,4S,7R,7aS)-2,2-dimethyl-5-[(4-methylphenyl)sulfonyl]-3a,4,7,7a-tetrahydro-4,7-epimino-1,3-benzodioxole-8-carboxylate 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: 96.0%

: 77-76-9
2,2-dimethoxy-propane

: (1S,4S,5S,6R)-5,6-Dihydroxy-2-(toluene-4-sulfonyl)-7-aza-bicyclo[2.2.1]hept-2-ene-7-carboxylic acid tert-butyl ester

: 205813-79-2
tert-butyl (3aR,4S,7R,7aS)-2,2-dimethyl-5-[(4-methylphenyl)sulfonyl]-3a,4,7,7a-tetrahydro-4,7-epimino-1,3-benzodioxole-8-carboxylate

Guidance literature:: With toluene-4-sulfonic acid; In acetone; for 3h; Ambient temperature;
DOI:10.1021/jo971907r

Reference yield: 90.0%

: 573716-76-4
(-)-(1S,2R,3S,4R,5S,6R)-7-tert-butoxycarbonyl-2,3-exo-isopropylidenedioxy-5-endo-methanesulfonyloxy-6-endo-p-toluenesulfonyl-7-azabicyclo[2.2.1]heptane

: 205813-79-2
tert-butyl (3aR,4S,7R,7aS)-2,2-dimethyl-5-[(4-methylphenyl)sulfonyl]-3a,4,7,7a-tetrahydro-4,7-epimino-1,3-benzodioxole-8-carboxylate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 25 ℃; for 0.25h;
DOI:10.1021/jo0301088

Reference yield:

: 5176-27-2
N-tert-butyloxycarbonyl-pyrrole

: 205813-79-2
tert-butyl (3aR,4S,7R,7aS)-2,2-dimethyl-5-[(4-methylphenyl)sulfonyl]-3a,4,7,7a-tetrahydro-4,7-epimino-1,3-benzodioxole-8-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 84 percent / 48 h / 80 - 85 °C

2: 47 percent / NaH / tetrahydrofuran / 2 h

3: 92 percent / MeMgBr / toluene; tetrahydrofuran / 0.08 h / Ambient temperature

4: 84 percent / NMO, OsO₄, NaHCO₃ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 6 h / Ambient temperature

5: 96 percent / p-TsOH*H₂O / acetone / 3 h / Ambient temperature

With osmium(VIII) oxide; N-methyl-2-indolinone; methylmagnesium bromide; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; In tetrahydrofuran; water; acetone; toluene; tert-butyl alcohol;
DOI:10.1021/jo971907r