Chloro-acetic acid (2R,4aR,6S,8S,8aS)-6-methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Base Information

• Chemical Name: Chloro-acetic acid (2R,4aR,6S,8S,8aS)-6-methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
• CAS No.: 161821-25-6
• Molecular Formula: C₁₉H₂₃ClO₆
• Molecular Weight: 382.841
• Mol file: 161821-25-6.mol

Synonyms:

Chemical Property of Chloro-acetic acid (2R,4aR,6S,8S,8aS)-6-methoxy-2-phenyl-7-prop-(Z)-ylidene-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 Chloro-acetic acid (2R,4aR,6S,8S,8aS)-6-methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

There total 2 articles about Chloro-acetic acid (2R,4aR,6S,8S,8aS)-6-methoxy-2-phenyl-7-prop-(Z)-ylidene-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: 37.0%

chloroacetic acid (79-11-8) + (2R,4aR,6S,8R,8aS)-6-Methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (161821-24-5) → Chloro-acetic acid (2R,4aR,6S,8S,8aS)-6-methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (161821-25-6) + Chloro-acetic acid (S)-1-((2R,4aR,6S,8aS)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-propyl ester (161821-28-9) + Chloro-acetic acid (R)-1-((2R,4aR,6S,8aS)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-propyl ester (161821-27-8)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In toluene; Yields of byproduct given;

DOI:10.1016/S0040-4039(00)73076-0

Reference yield:

(2R,4aR,6S,8aR)-6-Methoxy-2-phenyl-7-prop-(E)-ylidene-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one (114047-68-6) → Chloro-acetic acid (2R,4aR,6S,8S,8aS)-6-methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (161821-25-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / NaBH₄, CeCl₃ / ethanol

2: 37 percent / PPh₃, DEAD / toluene

With sodium tetrahydroborate; cerium(III) chloride; triphenylphosphine; diethylazodicarboxylate; In ethanol; toluene;

DOI:10.1016/S0040-4039(00)73076-0

Reference yield:

Chloro-acetic acid (2R,4aR,6S,8S,8aS)-6-methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (161821-25-6) → (2R,4aR,6S,8S,8aS)-6-Methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (161821-26-7)

Guidance literature:

With ammonia; In methanol; Yield given;

DOI:10.1016/S0040-4039(00)73076-0

upstream raw materials:

chloroacetic acid

(2R,4aR,6S,8R,8aS)-6-Methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

(2R,4aR,6S,8aR)-6-Methoxy-2-phenyl-7-prop-(E)-ylidene-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one

Downstream raw materials:

(2R,4aR,6S,8S,8aS)-6-Methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Bromomethyl-[(2R,4aR,6S,8S,8aR)-6-methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-dimethyl-silane