Pent-4-enoic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-pent-4-enoyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Pent-4-enoic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-pent-4-enoyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester
• CAS No.: 511274-61-6
• Molecular Formula: C₃₆H₄₀O₇S
• Molecular Weight: 616.775
• Mol file: 511274-61-6.mol

Synonyms:Pent-4-enoic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-pent-4-enoyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester

Chemical Property of Pent-4-enoic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-pent-4-enoyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Pent-4-enoic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-pent-4-enoyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester

There total 7 articles about Pent-4-enoic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-pent-4-enoyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yl 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: 90.0%

pent-4-enoic acid (591-80-0) + Phenyl 2,3-Di-O-benzyl-1-thio-β-D-glucopyranoside (129081-01-2) → Pent-4-enoic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-pent-4-enoyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester (511274-61-6)

Guidance literature:

pent-4-enoic acid; With dmap; benzotriazol-1-ol; diisopropyl-carbodiimide; In dichloromethane; for 1h;

Phenyl 2,3-Di-O-benzyl-1-thio-β-D-glucopyranoside; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 120h;

DOI:10.1021/jo051021k

Reference yield:

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol (2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-62-0,77481-63-1,105088-17-3,149495-84-1) → Pent-4-enoic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-pent-4-enoyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester (511274-61-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 74 percent / 10-camphorsulfonic acid / dimethylformamide / 48 h / 110 °C

2.1: 57 percent / NaH / 1,2-dimethoxy-ethane / 48 h / 20 °C

3.1: 97 percent / 10-camphorsulfonic acid / methanol / 48 h / 20 °C

4.1: 1,3-diisopropylcarbodiimide; 1-hydroxybenzotriazole; DMAP / CH₂Cl₂ / 1 h

4.2: 90 percent / CH₂Cl₂; dimethylformamide / 120 h / 20 °C

With dmap; (1S)-10-camphorsulfonic acid; sodium hydride; benzotriazol-1-ol; diisopropyl-carbodiimide; In methanol; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo051021k

Reference yield:

(2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (71676-30-7,87508-18-7,138922-03-9,87508-17-6) → Pent-4-enoic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-pent-4-enoyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester (511274-61-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 57 percent / NaH / 1,2-dimethoxy-ethane / 48 h / 20 °C

2.1: 97 percent / 10-camphorsulfonic acid / methanol / 48 h / 20 °C

3.1: 1,3-diisopropylcarbodiimide; 1-hydroxybenzotriazole; DMAP / CH₂Cl₂ / 1 h

3.2: 90 percent / CH₂Cl₂; dimethylformamide / 120 h / 20 °C

With dmap; (1S)-10-camphorsulfonic acid; sodium hydride; benzotriazol-1-ol; diisopropyl-carbodiimide; In methanol; 1,2-dimethoxyethane; dichloromethane;

DOI:10.1021/jo051021k

upstream raw materials:

pent-4-enoic acid

Phenyl 2,3-Di-O-benzyl-1-thio-β-D-glucopyranoside

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

(2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol