ethyl (1R,2S,3S,4S,6R)-6-(benzo[d][1,3]dioxol-5-yl)-2,3-dihydroxy-4-(triisopropylsilyloxy)cyclohexylcarbamate

Base Information

Chemical Name:ethyl (1R,2S,3S,4S,6R)-6-(benzo[d][1,3]dioxol-5-yl)-2,3-dihydroxy-4-(triisopropylsilyloxy)cyclohexylcarbamate
CAS No.:1309458-41-0
Molecular Formula:C₂₅H₄₁NO₇Si
Molecular Weight:495.689
Hs Code.:

Synonyms:ethyl (1R,2S,3S,4S,6R)-6-(benzo[d][1,3]dioxol-5-yl)-2,3-dihydroxy-4-(triisopropylsilyloxy)cyclohexylcarbamate

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Chemical Property of ethyl (1R,2S,3S,4S,6R)-6-(benzo[d][1,3]dioxol-5-yl)-2,3-dihydroxy-4-(triisopropylsilyloxy)cyclohexylcarbamate

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Technology Process of ethyl (1R,2S,3S,4S,6R)-6-(benzo[d][1,3]dioxol-5-yl)-2,3-dihydroxy-4-(triisopropylsilyloxy)cyclohexylcarbamate

There total 11 articles about ethyl (1R,2S,3S,4S,6R)-6-(benzo[d][1,3]dioxol-5-yl)-2,3-dihydroxy-4-(triisopropylsilyloxy)cyclohexylcarbamate 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: 95.0%

: 1309458-19-2
ethyl (1S,4S,6R)-6-(benzo[d][1,3]dioxol-5-yl)-4-(triisopropylsilyloxy)cyclohex-2-enylcarbamate

: 1309458-41-0
ethyl (1R,2S,3S,4S,6R)-6-(benzo[d][1,3]dioxol-5-yl)-2,3-dihydroxy-4-(triisopropylsilyloxy)cyclohexylcarbamate

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; at 20 ℃; for 15h; Darkness; Inert atmosphere;
DOI:10.1002/anie.201007135

Reference yield:

: 1019840-66-4
(1E,4E)-1-(benzo[d][1,3]dioxol-5-yl)deca-1,4-dien-3-one

: 1309458-41-0
ethyl (1R,2S,3S,4S,6R)-6-(benzo[d][1,3]dioxol-5-yl)-2,3-dihydroxy-4-(triisopropylsilyloxy)cyclohexylcarbamate

Guidance literature:: Multi-step reaction with 11 steps

1.1: bis(1,5-cyclooctadiene)nickel⁽⁰⁾; (S,S)-3,5-tBu₂PhTADDOLPPh / toluene / 15 h / 20 °C

2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 2 h / 20 °C / 760.05 Torr

3.1: cerium(III) chloride heptahydrate / tetrahydrofuran; methanol / 0.5 h / 0 °C / 760.05 Torr

3.2: 0.5 h / 0 °C

4.1: 2,4-dinitrobenzenesulfenyl chloride; triethylamine / 1,2-dichloro-ethane / 2.5 h / 83 °C / 760.05 Torr

5.1: [Pt(1,5-diphenylpenta-1,4-dien-3-one)3]; tricyclohexylphosphine / toluene / 15 h / 60 °C / Inert atmosphere

6.1: dihydrogen peroxide; sodium hydroxide / tetrahydrofuran; water / 4 h / 0 - 20 °C / 760.05 Torr

7.1: 2,6-dimethylpyridine; dihydrogen peroxide / dichloromethane / 1 h / 20 °C / Inert atmosphere

8.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -78 °C / Inert atmosphere

8.2: 0.5 h / -78 - 20 °C / Inert atmosphere

9.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide / tetrahydrofuran; water / 16 h / 20 °C / Inert atmosphere

10.1: triphenylphosphine / tetrahydrofuran; water / 14 h / 70 °C / Inert atmosphere

10.2: 9 h / 20 °C / Inert atmosphere

11.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water / 15 h / 20 °C / Darkness; Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dimethylpyridine; bis(1,5-cyclooctadiene)nickel⁽⁰⁾; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; sodium azide; [Pt(1,5-diphenylpenta-1,4-dien-3-one)3]; cerium(III) chloride heptahydrate; (S,S)-3,5-tBu₂PhTADDOLPPh; dihydrogen peroxide; 2,4-dinitrobenzenesulfenyl chloride; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; sodium hydroxide; tricyclohexylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; toluene; 3.1: Luche reduction / 3.2: Luche reduction / 10.1: Staudinger reaction / 10.2: Staudinger reaction;
DOI:10.1002/anie.201007135

Reference yield:

: (R,E)-4-(benzo[d][1,3]dioxol-5-yl)trideca-1,7-dien-6-one

: 1309458-41-0
ethyl (1R,2S,3S,4S,6R)-6-(benzo[d][1,3]dioxol-5-yl)-2,3-dihydroxy-4-(triisopropylsilyloxy)cyclohexylcarbamate

Guidance literature:: Multi-step reaction with 10 steps

1.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 2 h / 20 °C / 760.05 Torr

2.1: cerium(III) chloride heptahydrate / tetrahydrofuran; methanol / 0.5 h / 0 °C / 760.05 Torr

2.2: 0.5 h / 0 °C

3.1: 2,4-dinitrobenzenesulfenyl chloride; triethylamine / 1,2-dichloro-ethane / 2.5 h / 83 °C / 760.05 Torr

4.1: [Pt(1,5-diphenylpenta-1,4-dien-3-one)3]; tricyclohexylphosphine / toluene / 15 h / 60 °C / Inert atmosphere

5.1: dihydrogen peroxide; sodium hydroxide / tetrahydrofuran; water / 4 h / 0 - 20 °C / 760.05 Torr

6.1: 2,6-dimethylpyridine; dihydrogen peroxide / dichloromethane / 1 h / 20 °C / Inert atmosphere

7.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -78 °C / Inert atmosphere

7.2: 0.5 h / -78 - 20 °C / Inert atmosphere

8.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide / tetrahydrofuran; water / 16 h / 20 °C / Inert atmosphere

9.1: triphenylphosphine / tetrahydrofuran; water / 14 h / 70 °C / Inert atmosphere

9.2: 9 h / 20 °C / Inert atmosphere

10.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water / 15 h / 20 °C / Darkness; Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dimethylpyridine; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; sodium azide; [Pt(1,5-diphenylpenta-1,4-dien-3-one)3]; cerium(III) chloride heptahydrate; dihydrogen peroxide; 2,4-dinitrobenzenesulfenyl chloride; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; sodium hydroxide; tricyclohexylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; toluene; 2.1: Luche reduction / 2.2: Luche reduction / 9.1: Staudinger reaction / 9.2: Staudinger reaction;
DOI:10.1002/anie.201007135