(2S,3S,4S,5R)-3,4-Dihydroxy-2,5-bis-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,3S,4S,5R)-3,4-Dihydroxy-2,5-bis-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester
• CAS No.: 196494-77-6
• Molecular Formula: C₁₄H₁₉NO₆
• Molecular Weight: 297.308

Synonyms:

Chemical Property of (2S,3S,4S,5R)-3,4-Dihydroxy-2,5-bis-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S,5R)-3,4-Dihydroxy-2,5-bis-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

There total 12 articles about (2S,3S,4S,5R)-3,4-Dihydroxy-2,5-bis-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester 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:

3,5:6,7-bis-O-(1-methylethylidene)-α-D-glucoheptonic γ-lactone (6605-22-7) → (2S,3S,4S,5R)-3,4-Dihydroxy-2,5-bis-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester (196494-77-6)

Guidance literature:

Multi-step reaction with 12 steps

1: pyridine / CH₂Cl₂ / -20 °C

2: NaN₃ / dimethylformamide

3: CF₃COOH, H₂O

4: CSA / acetone

5: 91 percent / imidazole / dimethylformamide

6: 89 percent / pyridine / CH₂Cl₂

7: H₂ / Pd black / ethyl acetate

8: 94 percent / NaOAc / methanol

9: aq. NaHCO₃ / diethyl ether

10: CF₃COOH, H₂O

11: HIO₄ / tetrahydrofuran

12: NaBH₄ / ethanol

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium azide; camphor-10-sulfonic acid; water; hydrogen; sodium acetate; sodium hydrogencarbonate; periodic acid; trifluoroacetic acid; palladium; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(97)01539-6

Reference yield:

Trifluoro-methanesulfonic acid (4R,4aS,7R,7aR)-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-oxo-tetrahydro-furo[3,2-d][1,3]dioxin-7-yl ester (130481-75-3) → (2S,3S,4S,5R)-3,4-Dihydroxy-2,5-bis-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester (196494-77-6)

Guidance literature:

Multi-step reaction with 11 steps

1: NaN₃ / dimethylformamide

2: CF₃COOH, H₂O

3: CSA / acetone

4: 91 percent / imidazole / dimethylformamide

5: 89 percent / pyridine / CH₂Cl₂

6: H₂ / Pd black / ethyl acetate

7: 94 percent / NaOAc / methanol

8: aq. NaHCO₃ / diethyl ether

9: CF₃COOH, H₂O

10: HIO₄ / tetrahydrofuran

11: NaBH₄ / ethanol

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium azide; camphor-10-sulfonic acid; water; hydrogen; sodium acetate; sodium hydrogencarbonate; periodic acid; trifluoroacetic acid; palladium; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(97)01539-6

Reference yield:

2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-D-glycero-D-ido-heptono-1,4-lactone (191352-58-6) → (2S,3S,4S,5R)-3,4-Dihydroxy-2,5-bis-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester (196494-77-6)

Guidance literature:

Multi-step reaction with 10 steps

1: CF₃COOH, H₂O

2: CSA / acetone

3: 91 percent / imidazole / dimethylformamide

4: 89 percent / pyridine / CH₂Cl₂

5: H₂ / Pd black / ethyl acetate

6: 94 percent / NaOAc / methanol

7: aq. NaHCO₃ / diethyl ether

8: CF₃COOH, H₂O

9: HIO₄ / tetrahydrofuran

10: NaBH₄ / ethanol

With pyridine; 1H-imidazole; sodium tetrahydroborate; camphor-10-sulfonic acid; water; hydrogen; sodium acetate; sodium hydrogencarbonate; periodic acid; trifluoroacetic acid; palladium; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(97)01539-6

upstream raw materials:

3,5:6,7-bis-O-(1-methylethylidene)-α-D-glucoheptonic γ-lactone

Trifluoro-methanesulfonic acid (4R,4aS,7R,7aR)-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-oxo-tetrahydro-furo[3,2-d][1,3]dioxin-7-yl ester

2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-D-glycero-D-ido-heptono-1,4-lactone

(3S,4S,5R)-3-Azido-5-[(R)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-4-hydroxy-dihydro-furan-2-one

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