Bicyclo[2.2.1]heptane-2-carboxylic acid, 2-(acetylamino)-5,6-dihydroxy-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester, (1R,2S,4S,5S,6R)-

Base Information

• Chemical Name: Bicyclo[2.2.1]heptane-2-carboxylic acid, 2-(acetylamino)-5,6-dihydroxy-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester, (1R,2S,4S,5S,6R)-
• CAS No.: 915957-01-6
• Molecular Formula: C26H37NO5
• Molecular Weight: 443.583
• Mol file: 915957-01-6.mol

Synonyms:

Chemical Property of Bicyclo[2.2.1]heptane-2-carboxylic acid, 2-(acetylamino)-5,6-dihydroxy-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester, (1R,2S,4S,5S,6R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Bicyclo[2.2.1]heptane-2-carboxylic acid, 2-(acetylamino)-5,6-dihydroxy-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester, (1R,2S,4S,5S,6R)-

There total 1 articles about Bicyclo[2.2.1]heptane-2-carboxylic acid, 2-(acetylamino)-5,6-dihydroxy-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester, (1R,2S,4S,5S,6R)- 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: 90.0%

(1'R,3'R,4'S)-8'-phenylmenthyl (1S,2S,4S)-2-acetylamino-bicyclo[2.2.1]hept-5-ene-2-carboxylate (905733-12-2) → (1R,3R,4S)-8-phenylmenthyl (1R,2S,4S,5S,6R)-2-acetylamino-5,6-dihydroxybicyclo[2.2.1]heptane-2-carboxylate (915957-01-6)

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; at 20 ℃; for 8h;

DOI:10.1021/jo061391o

Reference yield:

(1R,3R,4S)-8-phenylmenthyl (1R,2S,4S,5S,6R)-2-acetylamino-5,6-dihydroxybicyclo[2.2.1]heptane-2-carboxylate (915957-01-6) → (1R,3R,4S)-8-phenylmenthyl (1S,2R,4S)-1-acetylamino-2,4-diformylcyclopentanecarboxylate (915957-05-0)

Guidance literature:

With sodium periodate; In 1,4-dioxane; water; at 20 ℃; for 2h;

DOI:10.1021/jo061391o

Reference yield:

(1R,3R,4S)-8-phenylmenthyl (1R,2S,4S,5S,6R)-2-acetylamino-5,6-dihydroxybicyclo[2.2.1]heptane-2-carboxylate (915957-01-6) → 6-amino-3-(4-methoxy-benzyl)-3-aza-bicyclo[3.2.1]octane-6-carboxylic acid (915957-17-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 395 mg / sodium periodate / dioxane; H₂O / 2 h / 20 °C

2: 57 percent / NaBH(OAc)3; AcOH / 1,2-dichloro-ethane / 4 h / 25 °C

3: 45 percent / MeONa / methanol / 50 h / 100 °C

With sodium periodate; sodium methylate; sodium tris(acetoxy)borohydride; acetic acid; In 1,4-dioxane; methanol; water; 1,2-dichloro-ethane;

DOI:10.1021/jo061391o

upstream raw materials:

(1'R,3'R,4'S)-8'-phenylmenthyl (1S,2S,4S)-2-acetylamino-bicyclo[2.2.1]hept-5-ene-2-carboxylate

Downstream raw materials:

(1R,3R,4S)-8-phenylmenthyl (1S,2R,4S)-1-acetylamino-2,4-diformylcyclopentanecarboxylate

6-amino-3-(4-methoxy-benzyl)-3-aza-bicyclo[3.2.1]octane-6-carboxylic acid

(1R,3R,4S)-8-phenylmenthyl (1S,5S,6R)-6-(acetylamino)-3-(4-methoxybenzyl)-3-azabicyclo[3.2.1]octane-6-carboxylate