(1S,6S)-6-benzyloxycarbonylaminocyclohex-3-enecarboxylic acid methyl ester

Base Information

• Chemical Name: (1S,6S)-6-benzyloxycarbonylaminocyclohex-3-enecarboxylic acid methyl ester
• CAS No.: 639814-85-0
• Molecular Formula: C₁₆H₁₉NO₄
• Molecular Weight: 289.331
• Mol file: 639814-85-0.mol

Synonyms:(1S,6S)-6-benzyloxycarbonylaminocyclohex-3-enecarboxylic acid methyl ester

Chemical Property of (1S,6S)-6-benzyloxycarbonylaminocyclohex-3-enecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,6S)-6-benzyloxycarbonylaminocyclohex-3-enecarboxylic acid methyl ester

There total 4 articles about (1S,6S)-6-benzyloxycarbonylaminocyclohex-3-enecarboxylic acid methyl ester 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:

(1S,2R)-2-(methoxycarbonyl)cyclohex-4-ene-1-carboxylic acid (31139-02-3,31139-03-4,56124-48-2,88335-93-7,88335-94-8,93603-11-3) + benzyl alcohol (100-51-6,185532-71-2) → (1S,6S)-6-benzyloxycarbonylaminocyclohex-3-enecarboxylic acid methyl ester (639814-85-0)

Guidance literature:

(1S,2R)-2-(methoxycarbonyl)cyclohex-4-ene-1-carboxylic acid; With potassium 2-methylbutan-2-olate; In toluene; at -15 ℃; Inert atmosphere;

benzyl alcohol; With diphenyl phosphoryl azide; triethylamine; In toluene; for 5h; Reflux; Inert atmosphere;

DOI:10.1039/c1ob05573a

Reference yield:

(1S,6S)-6-(2-oxooxazolidine-3-carbonyl)-cyclohex-3-enecarboxylic acid methyl ester (141435-12-3) → (1S,6S)-6-benzyloxycarbonylaminocyclohex-3-enecarboxylic acid methyl ester (639814-85-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LiOH*H₂O; H₂O₂ / tetrahydrofuran; H₂O / 17 h / 20 °C

2.1: diphenylphosphoryl azide / toluene / 3 h / 20 °C

3.1: toluene / 1.5 h / Heating

3.2: 1.43 g / toluene / 85 - 88 °C

With lithium hydroxide; diphenylphosphoranyl azide; dihydrogen peroxide; In tetrahydrofuran; water; toluene; 3.1: Curtius rearrangement;

DOI:10.1016/j.tetasy.2003.07.022

Reference yield:

(1S,2S)-Cyclohex-4-ene-1,2-dicarboxylic acid monomethyl ester (253454-00-1) → (1S,6S)-6-benzyloxycarbonylaminocyclohex-3-enecarboxylic acid methyl ester (639814-85-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: diphenylphosphoryl azide / toluene / 3 h / 20 °C

2.1: toluene / 1.5 h / Heating

2.2: 1.43 g / toluene / 85 - 88 °C

With diphenylphosphoranyl azide; In toluene; 2.1: Curtius rearrangement;

DOI:10.1016/j.tetasy.2003.07.022

upstream raw materials:

benzyl alcohol

(1S,6S)-6-(2-oxooxazolidine-3-carbonyl)-cyclohex-3-enecarboxylic acid methyl ester

(1S,2S)-Cyclohex-4-ene-1,2-dicarboxylic acid monomethyl ester

(1S,2R)-2-(methoxycarbonyl)cyclohex-4-ene-1-carboxylic acid

Downstream raw materials:

C₁₅H₁₇NO₄

C₂₀H₂₀N₂O₃S