(S)-2-Methyl-pent-4-enoic acid (4aR,6S,7R,8S,8aR)-6-methoxy-7-pent-4-enoyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Base Information

• Chemical Name: (S)-2-Methyl-pent-4-enoic acid (4aR,6S,7R,8S,8aR)-6-methoxy-7-pent-4-enoyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
• CAS No.: 808148-56-3
• Molecular Formula: C₂₅H₃₂O₈
• Molecular Weight: 460.524
• Mol file: 808148-56-3.mol

Synonyms:(S)-2-Methyl-pent-4-enoic acid (4aR,6S,7R,8S,8aR)-6-methoxy-7-pent-4-enoyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Chemical Property of (S)-2-Methyl-pent-4-enoic acid (4aR,6S,7R,8S,8aR)-6-methoxy-7-pent-4-enoyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Methyl-pent-4-enoic acid (4aR,6S,7R,8S,8aR)-6-methoxy-7-pent-4-enoyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

There total 3 articles about (S)-2-Methyl-pent-4-enoic acid (4aR,6S,7R,8S,8aR)-6-methoxy-7-pent-4-enoyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-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: 95.0%

(S)-2-methyl-4-pentenoic acid (20626-61-3) + Pent-4-enoic acid (4aR,6S,7R,8S,8aS)-8-hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (808148-55-2) → (S)-2-Methyl-pent-4-enoic acid (4aR,6S,7R,8S,8aR)-6-methoxy-7-pent-4-enoyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (808148-56-3)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃;

DOI:10.1021/ja048170p

Reference yield:

methyl 4,6-O-benzylidene-α-D-glucopyranoside (3162-96-7) → (S)-2-Methyl-pent-4-enoic acid (4aR,6S,7R,8S,8aR)-6-methoxy-7-pent-4-enoyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (808148-56-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Bu₂SnO / benzene; methanol / 12 h / 85 °C

1.2: 80 percent / dioxane / 20 °C

2.1: 95 percent / EDCI; DMAP / CH₂Cl₂ / 20 °C

With dmap; di(n-butyl)tin oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In methanol; dichloromethane; benzene;

DOI:10.1021/ja048170p

Reference yield:

pent-4-enoyl chloride (39716-58-0) → (S)-2-Methyl-pent-4-enoic acid (4aR,6S,7R,8S,8aR)-6-methoxy-7-pent-4-enoyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (808148-56-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Bu₂SnO / benzene; methanol / 12 h / 85 °C

1.2: 80 percent / dioxane / 20 °C

2.1: 95 percent / EDCI; DMAP / CH₂Cl₂ / 20 °C

With dmap; di(n-butyl)tin oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In methanol; dichloromethane; benzene;

DOI:10.1021/ja048170p

upstream raw materials:

(S)-2-methyl-4-pentenoic acid

Pent-4-enoic acid (4aR,6S,7R,8S,8aS)-8-hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

methyl 4,6-O-benzylidene-α-D-glucopyranoside

pent-4-enoyl chloride

Downstream raw materials:

(S)-2-Methyl-pent-4-enoic acid (2S,3R,4S,5R,6R)-2-methoxy-3,5-bis-pent-4-enoyloxy-6-trityloxymethyl-tetrahydro-pyran-4-yl ester

(S)-2-Methyl-pent-4-enoic acid (2R,3R,4S,5R,6S)-3-hydroxy-6-methoxy-5-pent-4-enoyloxy-2-trityloxymethyl-tetrahydro-pyran-4-yl ester