tert-butyl (2R)-2-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-methoxy-2-cyclohexen-1-yl]-2-hydroxyethylcarbamate

Base Information

• Chemical Name: tert-butyl (2R)-2-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-methoxy-2-cyclohexen-1-yl]-2-hydroxyethylcarbamate
• CAS No.: 945954-06-3
• Molecular Formula: C₂₈H₃₅NO₇
• Molecular Weight: 497.588

Synonyms:tert-butyl (2R)-2-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-methoxy-2-cyclohexen-1-yl]-2-hydroxyethylcarbamate

Chemical Property of tert-butyl (2R)-2-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-methoxy-2-cyclohexen-1-yl]-2-hydroxyethylcarbamate

Chemical Property:

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Technology Process of tert-butyl (2R)-2-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-methoxy-2-cyclohexen-1-yl]-2-hydroxyethylcarbamate

There total 14 articles about tert-butyl (2R)-2-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-methoxy-2-cyclohexen-1-yl]-2-hydroxyethylcarbamate 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: 99.0%

(1R)-2-azido-1-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-methoxy-2-cyclohexen-1-yl]-ethanol (945954-05-2) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (2R)-2-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-methoxy-2-cyclohexen-1-yl]-2-hydroxyethylcarbamate (945954-06-3)

Guidance literature:

With hydrogen; Lindlar's catalyst; In ethyl acetate; at 20 ℃; for 5h; atmospheric pressure;

DOI:10.1016/j.tet.2007.05.041

Reference yield:

(4S,6R)-4-benzyloxy-6-(tert-butyldimethylsilyloxy)-3-[3',4'-(methylenedioxy)phenyl]-2-cyclohexen-1-one (712280-92-7) → tert-butyl (2R)-2-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-methoxy-2-cyclohexen-1-yl]-2-hydroxyethylcarbamate (945954-06-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 1.87 g / CeCl₃*7H₂O; NaBH₄ / methanol; CH₂Cl₂ / 0.5 h / -78 °C

2.1: 71 percent / 2-nitrophenol; molecular sieves 4 Angstroem / 24 h / 130 °C

3.1: LiHMDS / tetrahydrofuran / 0.75 h / 0 °C

3.2: 38 percent / (1S)-(+)-(10-camphorsulfonyl)oxaziridine / tetrahydrofuran / 0.75 h / 0 °C

4.1: 90 percent / trimethyl borate; LiBH₄ / tetrahydrofuran / 4 h / 0 - 20 °C

5.1: 88 percent / triethylamine / CH₂Cl₂ / 4 h / 0 - 20 °C

6.1: 93 percent / Bu₄NF / tetrahydrofuran / 11 h / 0 - 20 °C

7.1: 92 percent / sodium hydride / tetrahydrofuran; various solvent(s) / 5 h / 0 °C

8.1: 79 percent / sodium azide; NH₄Cl / methanol / 48 h / 50 °C

9.1: 99 percent / hydrogen / Lindlar catalyst / ethyl acetate / 5 h / 20 °C / atmospheric pressure

With sodium tetrahydroborate; lithium borohydride; sodium azide; cerium(III) chloride; Trimethyl borate; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; ammonium chloride; triethylamine; 2-hydroxynitrobenzene; lithium hexamethyldisilazane; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; 1.1: Luche reduction / 2.1: Johnson-Claisen rearrangement;

DOI:10.1016/j.tet.2007.05.041

Reference yield:

(1R,4S,6R)-4-benzyloxy-6-(tert-butyldimethylsilyloxy)-3-[3',4'-(methylenedioxy)phenyl]-2-cyclohexen-1-ol (712280-93-8) → tert-butyl (2R)-2-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-methoxy-2-cyclohexen-1-yl]-2-hydroxyethylcarbamate (945954-06-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 71 percent / 2-nitrophenol; molecular sieves 4 Angstroem / 24 h / 130 °C

2.1: LiHMDS / tetrahydrofuran / 0.75 h / 0 °C

2.2: 38 percent / (1S)-(+)-(10-camphorsulfonyl)oxaziridine / tetrahydrofuran / 0.75 h / 0 °C

3.1: 90 percent / trimethyl borate; LiBH₄ / tetrahydrofuran / 4 h / 0 - 20 °C

4.1: 88 percent / triethylamine / CH₂Cl₂ / 4 h / 0 - 20 °C

5.1: 93 percent / Bu₄NF / tetrahydrofuran / 11 h / 0 - 20 °C

6.1: 92 percent / sodium hydride / tetrahydrofuran; various solvent(s) / 5 h / 0 °C

7.1: 79 percent / sodium azide; NH₄Cl / methanol / 48 h / 50 °C

8.1: 99 percent / hydrogen / Lindlar catalyst / ethyl acetate / 5 h / 20 °C / atmospheric pressure

With lithium borohydride; sodium azide; Trimethyl borate; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; ammonium chloride; triethylamine; 2-hydroxynitrobenzene; lithium hexamethyldisilazane; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; 1.1: Johnson-Claisen rearrangement;

DOI:10.1016/j.tet.2007.05.041

upstream raw materials:

(1R)-2-azido-1-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-methoxy-2-cyclohexen-1-yl]-ethanol

di-tert-butyl dicarbonate

(2R)-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-hydroxyacetic acid ethyl ester

(2S)-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-hydroxyacetic acid ethyl ester

Downstream raw materials:

tert-butyl (2R)-2-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-4-methoxy-6-hydroxy-2-cyclohexen-1-yl]-2-hydroxyethylcarbamate

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