(1R,2S,3S,4S,6R)-2,6-dimethyl-4-(phenylsulfonyl)-4-(2-propenyl)-3-<3-(tert-butoxycarbonyl)-2-oxopropyl>cyclohexane-1,2-diol 1,2-diacetonide

Base Information

• Chemical Name: (1R,2S,3S,4S,6R)-2,6-dimethyl-4-(phenylsulfonyl)-4-(2-propenyl)-3-<3-(tert-butoxycarbonyl)-2-oxopropyl>cyclohexane-1,2-diol 1,2-diacetonide
• CAS No.: 82769-94-6
• Molecular Formula: C₂₈H₄₀O₇S
• Molecular Weight: 520.687
• Mol file: 82769-94-6.mol

Synonyms:(1R,2S,3S,4S,6R)-2,6-dimethyl-4-(phenylsulfonyl)-4-(2-propenyl)-3-<3-(tert-butoxycarbonyl)-2-oxopropyl>cyclohexane-1,2-diol 1,2-diacetonide

Chemical Property of (1R,2S,3S,4S,6R)-2,6-dimethyl-4-(phenylsulfonyl)-4-(2-propenyl)-3-<3-(tert-butoxycarbonyl)-2-oxopropyl>cyclohexane-1,2-diol 1,2-diacetonide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,3S,4S,6R)-2,6-dimethyl-4-(phenylsulfonyl)-4-(2-propenyl)-3-<3-(tert-butoxycarbonyl)-2-oxopropyl>cyclohexane-1,2-diol 1,2-diacetonide

There total 3 articles about (1R,2S,3S,4S,6R)-2,6-dimethyl-4-(phenylsulfonyl)-4-(2-propenyl)-3-<3-(tert-butoxycarbonyl)-2-oxopropyl>cyclohexane-1,2-diol 1,2-diacetonide 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:

(1'S,1R,2R,3S,4S,6R)-2,6-dimethyl-3-<(((1'-phenylethyl)amino)carbonyl)oxy>-4-(phenylsulfonyl)cyclohexane-1,2-diol 1,2-acetonide (82769-87-7) → (1R,2S,3S,4S,6R)-2,6-dimethyl-4-(phenylsulfonyl)-4-(2-propenyl)-3-<3-(tert-butoxycarbonyl)-2-oxopropyl>cyclohexane-1,2-diol 1,2-diacetonide (82769-94-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / Heating

2: 1.) KDA / 1.) THF, 40 min, 2.) -25 deg C, 30 min

With Diethoxy-methyl-(6-amino-hexylaminomethyl)-silan; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran;

DOI:10.1021/ja00385a030

Reference yield:

((S)-1-Phenyl-ethyl)-carbamic acid 2,2,3a,7-tetramethyl-5-phenylsulfanyl-hexahydro-benzo[1,3]dioxol-4-yl ester (82769-84-4,82769-85-5) → (1R,2S,3S,4S,6R)-2,6-dimethyl-4-(phenylsulfonyl)-4-(2-propenyl)-3-<3-(tert-butoxycarbonyl)-2-oxopropyl>cyclohexane-1,2-diol 1,2-diacetonide (82769-94-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 15.0 g / m-chloroperbenzoic acid / CH₂Cl₂ / 1.) -35 deg C, 10 min, 2.) -35 deg C -> 25 deg C, 1 h

2: 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / Heating

3: 1.) KDA / 1.) THF, 40 min, 2.) -25 deg C, 30 min

With Diethoxy-methyl-(6-amino-hexylaminomethyl)-silan; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00385a030

Reference yield:

tert-butyl acetoacetate (1694-31-1) + (1R,2S,6R)-2,6-dimethyl-4-(phenylsulfonyl)cyclohex-3-ene-1,2-diol 1,2-diacetonide (82796-49-4) + allyl bromide (106-95-6) → (1R,2S,3S,4S,6R)-2,6-dimethyl-4-(phenylsulfonyl)-4-(2-propenyl)-3-<3-(tert-butoxycarbonyl)-2-oxopropyl>cyclohexane-1,2-diol 1,2-diacetonide (82769-94-6)

Guidance literature:

With Diethoxy-methyl-(6-amino-hexylaminomethyl)-silan; Yield given. Multistep reaction; 1.) THF, 40 min, 2.) -25 deg C, 30 min;

DOI:10.1021/ja00385a030

upstream raw materials:

tert-butyl acetoacetate

(1R,2S,6R)-2,6-dimethyl-4-(phenylsulfonyl)cyclohex-3-ene-1,2-diol 1,2-diacetonide

allyl bromide

((S)-1-Phenyl-ethyl)-carbamic acid 2,2,3a,7-tetramethyl-5-phenylsulfanyl-hexahydro-benzo[1,3]dioxol-4-yl ester

Downstream raw materials:

(3aR,4R,5aS,6R,10aR)-6-Benzoyloxy-2,2,4,10b-tetramethyl-9-oxo-4,5,5a,6,9,10,10a,10b-octahydro-3aH-1,3-dioxa-cyclohepta[e]indene-8-carboxylic acid

C₂₄H₂₈O₇

C₂₈H₃₆O₇

(1S,2R,3S,5R,6R,7S,8R,10R,11S,14R,15S,18R)-13,14-dibenzyl-18-(2-(trimethylsilyl)ethoxy)-6,7,10-trihydroxy-5,7,16,17-tetramethyl-12-oxo-13-aza-19-oxapentacyclo<9.7.0^2,10.0^3,8.0^11,15>nonadec-16-ene 6,7-acetonide