(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
Hs Code.:

(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

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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

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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:

: 110414-90-9
α-N-tosyl-δ-N-carbobenzoxyornthine

: 124376-12-1
(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

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:

: 124288-73-9
1,1-dimethylethyl (S)-2-<<(4-methylphenyl)sulfonyl>-amino>-5-<<(phenylmethoxy)carbonyl>amino>pentanoate

: 124376-12-1
(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

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:

: 33985-40-9
(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde

: 124376-12-1
(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

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