(1'S,1S,2S,3R,4R,6S)-2,6-dimethyl-3-<(((1'-phenylethyl)amino)carbonyl)oxy>-4-(phenylthio)cyclohexane-1,2-diol 1,2-acetonide

Base Information

• Chemical Name: (1'S,1S,2S,3R,4R,6S)-2,6-dimethyl-3-<(((1'-phenylethyl)amino)carbonyl)oxy>-4-(phenylthio)cyclohexane-1,2-diol 1,2-acetonide
• CAS No.: 82769-84-4
• Molecular Formula: C₂₆H₃₃NO₄S
• Molecular Weight: 455.618
• Mol file: 82769-84-4.mol

Synonyms:

Chemical Property of (1'S,1S,2S,3R,4R,6S)-2,6-dimethyl-3-<(((1'-phenylethyl)amino)carbonyl)oxy>-4-(phenylthio)cyclohexane-1,2-diol 1,2-acetonide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'S,1S,2S,3R,4R,6S)-2,6-dimethyl-3-<(((1'-phenylethyl)amino)carbonyl)oxy>-4-(phenylthio)cyclohexane-1,2-diol 1,2-acetonide

There total 1 articles about (1'S,1S,2S,3R,4R,6S)-2,6-dimethyl-3-<(((1'-phenylethyl)amino)carbonyl)oxy>-4-(phenylthio)cyclohexane-1,2-diol 1,2-acetonide 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: 15.0%

(-)-(S)-(α-methylbenzyl)isocyanate (14649-03-7) + trans,cis-3,5-dimethyl-1-phenylthio-trans,cis,cis-2,3,4-trihydroxycyclohexane 3,4-acetonide (81939-86-8) → (1'S,1R,2R,3S,4S,6R)-2,6-dimethyl-3-<(((1'-phenylethyl)amino)carbonyl)oxy>-4-(phenylthio)cyclohexane-1,2-diol 1,2-acetonide (82769-85-5) + (1'S,1S,2S,3R,4R,6S)-2,6-dimethyl-3-<(((1'-phenylethyl)amino)carbonyl)oxy>-4-(phenylthio)cyclohexane-1,2-diol 1,2-acetonide (82769-84-4)

Guidance literature:

at 140 ℃; for 18h;

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) → (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<9.7.02,10.03,8.011,15>nonadec-16-ene 6,7-acetonide (82770-11-4)

Guidance literature:

Multi-step reaction with 10 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

4: 1.) potassium tert-butoxide, 2.) ammoniua, lithium / 1.) tert-butyl alcohol, THF, 0 deg C, 5 min, 2.) -78 deg C, 1.5 h

6: 1.) 80percent m-chloroperbenzoic acid, sodium bicarbonate / 1.) methylene chloride, 0 deg C, 25 min, 2.) pyridine, 25 deg C, 3 h

7: 94 percent / methanesulfonic acid, trifluoroacetic acid / CH₂Cl₂ / 2 h / 25 °C

8: 78 percent / 1 h / 25 °C

9: 67 percent / toluene / 36 h / 110 °C

10: 96 percent / potassium tert-butoxide / H₂O; diethyl ether / 20 h / 25 °C

With methanesulfonic acid; Diethoxy-methyl-(6-amino-hexylaminomethyl)-silan; potassium tert-butylate; ammonia; lithium; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene;

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) → (1S,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-2,12-dioxo-13-azatetracyclo<9.7.0.03,8.011,15>octadec-16-ene 6,7-acetonide (82770-13-6)

Guidance literature:

Multi-step reaction with 12 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

4: 1.) potassium tert-butoxide, 2.) ammoniua, lithium / 1.) tert-butyl alcohol, THF, 0 deg C, 5 min, 2.) -78 deg C, 1.5 h

6: 1.) 80percent m-chloroperbenzoic acid, sodium bicarbonate / 1.) methylene chloride, 0 deg C, 25 min, 2.) pyridine, 25 deg C, 3 h

7: 94 percent / methanesulfonic acid, trifluoroacetic acid / CH₂Cl₂ / 2 h / 25 °C

8: 78 percent / 1 h / 25 °C

9: 67 percent / toluene / 36 h / 110 °C

10: 96 percent / potassium tert-butoxide / H₂O; diethyl ether / 20 h / 25 °C

11: 85 percent / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 4 h / 25 °C

12: 1.) L-Selectride, 2.) 5percent aq. sodium hydroxide, 30percent hydrogen peroxide / 1.) THF, -78 deg C, 1 h, 2.) 0 deg C, 10 min

With sodium hydroxide; methanesulfonic acid; Diethoxy-methyl-(6-amino-hexylaminomethyl)-silan; potassium tert-butylate; ammonia; dihydrogen peroxide; sodium acetate; lithium; L-Selectride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene;

DOI:10.1021/ja00385a030

upstream raw materials:

(-)-(S)-(α-methylbenzyl)isocyanate

trans,cis-3,5-dimethyl-1-phenylthio-trans,cis,cis-2,3,4-trihydroxycyclohexane 3,4-acetonide

Downstream raw materials:

(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

(1'S,1S,2S,3R,4R,6S)-2,6-dimethyl-3-<(((1'-phenylethyl)amino)carbonyl)oxy>-4-(phenylsulfonyl)cyclohexane-1,2-diol 1,2-acetonide

(3αS,4S,7αR)-2,2,4,7α-tetramethyl-6-(phenylsulfonyl)-3α,4,5,7α-tetrahydrobenzo[δ][1,3]dioxole

(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