(2R)-cis-methyl <5-deoxy-5-<5-(1,1-dimethylethoxy)-carbonyl>-1-<(4-methylphenyl)sulfonyl>-2-pyrrolidinyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranoside

Base Information

• Chemical Name: (2R)-cis-methyl <5-deoxy-5-<5-(1,1-dimethylethoxy)-carbonyl>-1-<(4-methylphenyl)sulfonyl>-2-pyrrolidinyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranoside
• CAS No.: 124376-12-1
• Molecular Formula: C₂₅H₃₇NO₈S
• Molecular Weight: 511.637
• Mol file: 124376-12-1.mol

Synonyms:

Chemical Property of (2R)-cis-methyl <5-deoxy-5-<5-(1,1-dimethylethoxy)-carbonyl>-1-<(4-methylphenyl)sulfonyl>-2-pyrrolidinyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-cis-methyl <5-deoxy-5-<5-(1,1-dimethylethoxy)-carbonyl>-1-<(4-methylphenyl)sulfonyl>-2-pyrrolidinyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranoside

There total 9 articles about (2R)-cis-methyl <5-deoxy-5-<5-(1,1-dimethylethoxy)-carbonyl>-1-<(4-methylphenyl)sulfonyl>-2-pyrrolidinyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranoside 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:

α-N-tosyl-δ-N-carbobenzoxyornthine (110414-90-9) → (2R)-cis-methyl <5-deoxy-5-<5-(1,1-dimethylethoxy)-carbonyl>-1-<(4-methylphenyl)sulfonyl>-2-pyrrolidinyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranoside (124376-12-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 82 percent / CHCl₃ / 22 h / 22 °C

2: 99 percent / H₂ / 10percent Pd/C / methanol / 3102.9 Torr

3: 56 percent / m-CPBA / CH₂Cl₂ / 0.28 h / Heating

4: 86 percent / KF / acetonitrile / 24 h / 22 °C

5: 96 percent / dicyclohexylcarbodiimde, copper(I) chloride / acetonitrile / 16 h / 35 °C

6: 84 percent / zinc dust, acetic acid / tetrahydrofuran / 0.25 h / 45 °C

7: 81 percent / cerium(IV) ammonium nitrate, HNO₃ / ethanol / 0.25 h / -42 °C

8: 80 percent / L-selectride / tetrahydrofuran / 2 h / -78 °C

9: 1) pyridine, 2) sodium hydride / 0 deg C, 1) 40 min, 2) THF, 3 h

With pyridine; potassium fluoride; ammonium cerium(IV) nitrate; hydrogen; nitric acid; L-Selectride; sodium hydride; acetic acid; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; copper(l) chloride; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; acetonitrile;

DOI:10.1021/jo00290a028

Reference yield:

1,1-dimethylethyl (S)-2-<<(4-methylphenyl)sulfonyl>-amino>-5-<<(phenylmethoxy)carbonyl>amino>pentanoate (124288-73-9) → (2R)-cis-methyl <5-deoxy-5-<5-(1,1-dimethylethoxy)-carbonyl>-1-<(4-methylphenyl)sulfonyl>-2-pyrrolidinyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranoside (124376-12-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 99 percent / H₂ / 10percent Pd/C / methanol / 3102.9 Torr

2: 56 percent / m-CPBA / CH₂Cl₂ / 0.28 h / Heating

3: 86 percent / KF / acetonitrile / 24 h / 22 °C

4: 96 percent / dicyclohexylcarbodiimde, copper(I) chloride / acetonitrile / 16 h / 35 °C

5: 84 percent / zinc dust, acetic acid / tetrahydrofuran / 0.25 h / 45 °C

6: 81 percent / cerium(IV) ammonium nitrate, HNO₃ / ethanol / 0.25 h / -42 °C

7: 80 percent / L-selectride / tetrahydrofuran / 2 h / -78 °C

8: 1) pyridine, 2) sodium hydride / 0 deg C, 1) 40 min, 2) THF, 3 h

With pyridine; potassium fluoride; ammonium cerium(IV) nitrate; hydrogen; nitric acid; L-Selectride; sodium hydride; acetic acid; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; copper(l) chloride; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetonitrile;

DOI:10.1021/jo00290a028

Reference yield:

(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde (33985-40-9) → (2R)-cis-methyl <5-deoxy-5-<5-(1,1-dimethylethoxy)-carbonyl>-1-<(4-methylphenyl)sulfonyl>-2-pyrrolidinyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranoside (124376-12-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 86 percent / KF / acetonitrile / 24 h / 22 °C

2: 96 percent / dicyclohexylcarbodiimde, copper(I) chloride / acetonitrile / 16 h / 35 °C

3: 84 percent / zinc dust, acetic acid / tetrahydrofuran / 0.25 h / 45 °C

4: 81 percent / cerium(IV) ammonium nitrate, HNO₃ / ethanol / 0.25 h / -42 °C

5: 80 percent / L-selectride / tetrahydrofuran / 2 h / -78 °C

6: 1) pyridine, 2) sodium hydride / 0 deg C, 1) 40 min, 2) THF, 3 h

With pyridine; potassium fluoride; ammonium cerium(IV) nitrate; nitric acid; L-Selectride; sodium hydride; acetic acid; dicyclohexyl-carbodiimide; copper(l) chloride; zinc; In tetrahydrofuran; ethanol; acetonitrile;

DOI:10.1021/jo00290a028

upstream raw materials:

(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde

1,1-dimethylethyl (S)-5-amino-2-<<(4-methylphenyl)sulfonyl>-amino>pentanoate

1,1-dimethylethyl (S)-5-nitro-2-<<(4-methylphenyl)sulfonyl>amino>pentanoate

α-N-tosyl-δ-N-carbobenzoxyornthine