1'-C-[(4S,5R)-1,2-dimethyl-4-(2''-methoxycarbonylethyl)-4-nitrocyclohex-1-en-5-yl]-D-manno-pentitol

Base Information

• Chemical Name: 1'-C-[(4S,5R)-1,2-dimethyl-4-(2''-methoxycarbonylethyl)-4-nitrocyclohex-1-en-5-yl]-D-manno-pentitol
• CAS No.: 501665-22-1
• Molecular Formula: C₁₇H₂₉NO₉
• Molecular Weight: 391.419
• Mol file: 501665-22-1.mol

Synonyms:1'-C-[(4S,5R)-1,2-dimethyl-4-(2''-methoxycarbonylethyl)-4-nitrocyclohex-1-en-5-yl]-D-manno-pentitol

Chemical Property of 1'-C-[(4S,5R)-1,2-dimethyl-4-(2''-methoxycarbonylethyl)-4-nitrocyclohex-1-en-5-yl]-D-manno-pentitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1'-C-[(4S,5R)-1,2-dimethyl-4-(2''-methoxycarbonylethyl)-4-nitrocyclohex-1-en-5-yl]-D-manno-pentitol

There total 2 articles about 1'-C-[(4S,5R)-1,2-dimethyl-4-(2''-methoxycarbonylethyl)-4-nitrocyclohex-1-en-5-yl]-D-manno-pentitol 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: 69.0%

1',2',3',4',5'-penta-O-acetyl-1'-C-[(4S,5R)-1,2-dimethyl-4-(2''-methoxycarbonylethyl)-4-nitrocyclohex-1-en-5-yl]-D-manno-pentitol (217298-50-5) → 1'-C-[(4S,5R)-1,2-dimethyl-4-(2''-methoxycarbonylethyl)-4-nitrocyclohex-1-en-5-yl]-D-manno-pentitol (501665-22-1)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 24h;

DOI:10.1016/S0957-4166(02)00416-0

Reference yield:

1',2',3',4',5'-penta-O-acetyl-1'-C-[(4R,5R)-1,2-dimethyl-4-nitrocyclohex-1-en-5-yl]-D-manno-pentitol (438625-50-4) → 1'-C-[(4S,5R)-1,2-dimethyl-4-(2''-methoxycarbonylethyl)-4-nitrocyclohex-1-en-5-yl]-D-manno-pentitol (501665-22-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / DBU / acetonitrile / 12 h / 20 °C

2: 69 percent / NaOMe / methanol / 24 h / 20 °C

With sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; acetonitrile; 1: Michael addition;

DOI:10.1016/S0957-4166(02)00416-0

Reference yield: 68.0%

1'-C-[(4S,5R)-1,2-dimethyl-4-(2''-methoxycarbonylethyl)-4-nitrocyclohex-1-en-5-yl]-D-manno-pentitol (501665-22-1) → (4S,5R)-5-formyl-1,2-dimethyl-4-(2''-methoxycarbonylethyl)-4-nitrocyclohex-1-ene

Guidance literature:

With sodium periodate; In water; at 0 ℃; for 0.25h;

DOI:10.1016/S0957-4166(02)00416-0

upstream raw materials:

1',2',3',4',5'-penta-O-acetyl-1'-C-[(4S,5R)-1,2-dimethyl-4-(2''-methoxycarbonylethyl)-4-nitrocyclohex-1-en-5-yl]-D-manno-pentitol

1',2',3',4',5'-penta-O-acetyl-1'-C-[(4R,5R)-1,2-dimethyl-4-nitrocyclohex-1-en-5-yl]-D-manno-pentitol