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

Base Information

Chemical Name: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
CAS No.:808148-55-2
Molecular Formula:C₁₉H₂₄O₇
Molecular Weight:364.395
Hs Code.:

Synonyms: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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 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

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Technology Process of 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

There total 1 articles about 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 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: 80.0%

: 3162-96-7
methyl 4,6-O-benzylidene-α-D-glucopyranoside

: 39716-58-0
pent-4-enoyl chloride

: 808148-55-2
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

Guidance literature:: methyl 4,6-O-benzylidene-α-D-glucopyranoside; With di(n-butyl)tin oxide; In methanol; benzene; at 85 ℃; for 12h;

pent-4-enoyl chloride; In 1,4-dioxane; at 20 ℃;
DOI:10.1021/ja048170p

Reference yield: 95.0%

: 20626-61-3
(S)-2-methyl-4-pentenoic acid

: 808148-55-2
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

: 808148-56-3
(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

Guidance literature:: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃;
DOI:10.1021/ja048170p

Reference yield:

: 808148-55-2
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

: 808148-57-4
(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

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / EDCI; DMAP / CH₂Cl₂ / 20 °C

2: aq. AcOH / 10 h / 80 °C

3: DMAP; pyridine / 15 h / 80 °C

With pyridine; dmap; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;
DOI:10.1021/ja048170p