1H-Azepine-1-carboxylic acid, 2,3,4,7-tetrahydro-3,4-bis(phenylmethoxy)-2-[(phenylmethoxy)methyl]-, phenylmethyl ester, (2S,3R,4R)-

Base Information

• Chemical Name: 1H-Azepine-1-carboxylic acid, 2,3,4,7-tetrahydro-3,4-bis(phenylmethoxy)-2-[(phenylmethoxy)methyl]-, phenylmethyl ester, (2S,3R,4R)-
• CAS No.: 724705-55-9
• Molecular Formula: C36H37NO5
• Molecular Weight: 563.693
• Mol file: 724705-55-9.mol

Synonyms:

Chemical Property of 1H-Azepine-1-carboxylic acid, 2,3,4,7-tetrahydro-3,4-bis(phenylmethoxy)-2-[(phenylmethoxy)methyl]-, phenylmethyl ester, (2S,3R,4R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1H-Azepine-1-carboxylic acid, 2,3,4,7-tetrahydro-3,4-bis(phenylmethoxy)-2-[(phenylmethoxy)methyl]-, phenylmethyl ester, (2S,3R,4R)-

There total 2 articles about 1H-Azepine-1-carboxylic acid, 2,3,4,7-tetrahydro-3,4-bis(phenylmethoxy)-2-[(phenylmethoxy)methyl]-, phenylmethyl ester, (2S,3R,4R)- 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:

benzyl chloroformate (501-53-1,94274-21-2) → (2S,3R,5R)-N-benzyloxycarbonyl-2-benzyloxymethyl-3,4-dibenzyloxy-5,6-didehydro-azepane (724705-55-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / aq. KHCO₃ / ethyl acetate

2: 84 percent / Grubbs' catalyst / CH₂Cl₂ / 76 h / 45 °C

With potassium hydrogencarbonate; Grubbs catalyst first generation; In dichloromethane; ethyl acetate;

DOI:10.1039/b402542c

Reference yield:

(3R,4R,5S)-5-allylamino-3,4,6-tribenzyloxy-hex-1-ene (724705-46-8) → (2S,3R,5R)-N-benzyloxycarbonyl-2-benzyloxymethyl-3,4-dibenzyloxy-5,6-didehydro-azepane (724705-55-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / aq. KHCO₃ / ethyl acetate

2: 84 percent / Grubbs' catalyst / CH₂Cl₂ / 76 h / 45 °C

With potassium hydrogencarbonate; Grubbs catalyst first generation; In dichloromethane; ethyl acetate;

DOI:10.1039/b402542c

Reference yield: 42.0%

(2S,3R,5R)-N-benzyloxycarbonyl-2-benzyloxymethyl-3,4-dibenzyloxy-5,6-didehydro-azepane (724705-55-9) → (1S,4S,5R,6S,7S)-5,6-Bis-benzyloxy-4-benzyloxymethyl-8-oxa-3-aza-bicyclo[5.1.0]octane-3-carboxylic acid benzyl ester (848909-06-8) + (1R,4S,5R,6S,7R)-5,6-Bis-benzyloxy-4-benzyloxymethyl-8-oxa-3-aza-bicyclo[5.1.0]octane-3-carboxylic acid benzyl ester (848909-01-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1016/j.tetasy.2004.12.005

upstream raw materials:

benzyl chloroformate

(3R,4R,5S)-5-allylamino-3,4,6-tribenzyloxy-hex-1-ene

Downstream raw materials:

(2S,3R,4R,5R,6R)-N-benzyloxycarbonyl-2-benzyloxymethyl-3,4-dibenzyloxy-5,6-dihydroxy-azepane

(2S,3R,4R,5S,6S)-N-benzyloxycarbonyl-2-benzyloxymethyl-3,4-dibenzyloxy-5,6-dihydroxy-azepane

(1S,4S,5R,6S,7S)-5,6-Bis-benzyloxy-4-benzyloxymethyl-8-oxa-3-aza-bicyclo[5.1.0]octane-3-carboxylic acid benzyl ester

(1R,4S,5R,6S,7R)-5,6-Bis-benzyloxy-4-benzyloxymethyl-8-oxa-3-aza-bicyclo[5.1.0]octane-3-carboxylic acid benzyl ester