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

Base Information

• Chemical Name: (1R,6R)-6-benzyloxycarbonylaminocyclohex-3-enecarboxylic acid methyl ester
• CAS No.: 91280-45-4
• Molecular Formula: C₁₆H₁₉NO₄
• Molecular Weight: 289.331
• Mol file: 91280-45-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 17 articles about (1R,6R)-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: 96.0%

methyl (2R,3R)-2-allyl-3-[(benzyloxy)carbonylamino]hex-5-enoate (475291-71-5) → (1R,6R)-6-benzyloxycarbonylaminocyclohex-3-enecarboxylic acid methyl ester (91280-45-4)

Guidance literature:

With Grubbs catalyst first generation; In benzene; for 2h; Heating;

DOI:10.1021/jo049794g

Reference yield: 72.0%

(1S,6R)-6-Benzyloxycarbonylamino-cyclohex-3-ene-1-carboxylic acid methyl ester (91259-90-4) → (1R,6R)-6-benzyloxycarbonylaminocyclohex-3-enecarboxylic acid methyl ester (91280-45-4)

Guidance literature:

With sodium methylate; In methanol; for 6h; Heating;

DOI:10.1016/S0040-4039(01)81230-2

Reference yield:

methyl (3R)-3-[(benzyloxy)carbonylamino]hex-5-enoate (81576-71-8) → (1R,6R)-6-benzyloxycarbonylaminocyclohex-3-enecarboxylic acid methyl ester (91280-45-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 49 percent / LDA; LiCl / tetrahydrofuran / 18 h / -78 - 20 °C

2: 96 percent / Grubbs' ruthenium catalyst / benzene / 2 h / Heating

With Grubbs catalyst first generation; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; benzene;

DOI:10.1021/jo049794g

upstream raw materials:

(1S,6R)-6-Benzyloxycarbonylamino-cyclohex-3-ene-1-carboxylic acid methyl ester

methyl (2R,3R)-2-allyl-3-[(benzyloxy)carbonylamino]hex-5-enoate

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

benzyl alcohol

Downstream raw materials:

(1R,6R)-6-benzyloxycarbonylaminocyclohex-3-enecarboxylic acid

(1R,2R)-2-aminocyclohexanecarboxylic acid methyl ester

(1R,2R,4S,5S)-2-benzyloxycarbonylamino-4-iodo-7-oxo-6-oxabicyclo<3.2.1>octane

C₂₀H₂₀N₂O₃S