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

Base Information

• Chemical Name: (2R,4aR,6S,8R,8aS)-6-Methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol
• CAS No.: 161821-24-5
• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.359
• Mol file: 161821-24-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (2R,4aR,6S,8R,8aS)-6-Methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol 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: 73.0%

(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) → (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)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In ethanol;

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

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,8R,8aS)-6-Methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (161821-24-5) → (1S,4aS,4bS,6R,8aR,10S,10aS)-1-Ethyl-10-methoxy-3,3-dimethyl-6-phenyl-octahydro-2,5,7,9-tetraoxa-3-sila-phenanthrene

Guidance literature:

Multi-step reaction with 4 steps

1: PPh₃, DEAD / toluene

2: NH₃ / methanol

3: Et₃N / CH₂Cl₂

4: 74 percent / Bu₃SnH, AIBN / benzene / 3 h / Heating

With 2,2'-azobis(isobutyronitrile); ammonia; tri-n-butyl-tin hydride; triethylamine; triphenylphosphine; diethylazodicarboxylate; In methanol; dichloromethane; toluene; benzene;

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

upstream raw materials:

(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:

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

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

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

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