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

Base Information

• Chemical Name: 1'-C-[(4R,5S)-1,2-dimethyl-4-(2''-methoxycarbonylethyl)-4-nitrocyclohex-1-en-5-yl]-D-galacto-pentitol
• CAS No.: 501665-20-9
• Molecular Formula: C₁₇H₂₉NO₉
• Molecular Weight: 391.419

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

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

Chemical Property:

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

There total 3 articles about 1'-C-[(4R,5S)-1,2-dimethyl-4-(2''-methoxycarbonylethyl)-4-nitrocyclohex-1-en-5-yl]-D-galacto-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: 93.0%

1',2',3',4',5'-penta-O-acetyl-1'-C-[(4R,5S)-1,2-dimethyl-4-(2''-methoxycarbonylethyl)-4-nitrocyclohex-1-en-5-yl]-D-galacto-pentitol (217298-43-6) → 1'-C-[(4R,5S)-1,2-dimethyl-4-(2''-methoxycarbonylethyl)-4-nitrocyclohex-1-en-5-yl]-D-galacto-pentitol (501665-20-9)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 12h;

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

Reference yield:

1',2',3',4',5'-penta-O-acetyl-1'-C-[(4S,5S)-1,2-dimethyl-4-nitrocyclohex-1-en-5-yl]-D-galacto-pentitol (125517-80-8) → 1'-C-[(4R,5S)-1,2-dimethyl-4-(2''-methoxycarbonylethyl)-4-nitrocyclohex-1-en-5-yl]-D-galacto-pentitol (501665-20-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / DBU / acetonitrile / 24 h / 20 °C

2: 93 percent / NaOMe / methanol / 12 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:

(4R,5S)-1,2,3,4,5-penta-O-acetyl-1-C-(1,2-dimethyl-4-nitrocyclohex-1-en-5-yl)-D-galacto-pentitol (139406-35-2) → 1'-C-[(4R,5S)-1,2-dimethyl-4-(2''-methoxycarbonylethyl)-4-nitrocyclohex-1-en-5-yl]-D-galacto-pentitol (501665-20-9)

Guidance literature:

Multi-step reaction with 2 steps

1: DBU / acetonitrile

2: 93 percent / NaOMe / methanol / 12 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

upstream raw materials:

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

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

(4R,5S)-1,2,3,4,5-penta-O-acetyl-1-C-(1,2-dimethyl-4-nitrocyclohex-1-en-5-yl)-D-galacto-pentitol

Downstream raw materials:

(4R,5S)-5-formyl-1,2-dimethyl-4-(2''-methoxycarbonylethyl)-4-nitrocyclohex-1-ene

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