(E)-3-Phenyl-acrylic acid (1aS,1bS,2S,5aR,6S,6aS)-6-acetoxy-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1b,5a,6,6a-tetrahydro-2H-1,3-dioxa-cyclopropa[a]inden-1a-ylmethyl ester

Base Information

• Chemical Name: (E)-3-Phenyl-acrylic acid (1aS,1bS,2S,5aR,6S,6aS)-6-acetoxy-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1b,5a,6,6a-tetrahydro-2H-1,3-dioxa-cyclopropa[a]inden-1a-ylmethyl ester
• CAS No.: 31939-25-0
• Molecular Formula: C₃₄H₃₈O₁₆
• Molecular Weight: 702.666
• Mol file: 31939-25-0.mol

Synonyms:

Chemical Property of (E)-3-Phenyl-acrylic acid (1aS,1bS,2S,5aR,6S,6aS)-6-acetoxy-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1b,5a,6,6a-tetrahydro-2H-1,3-dioxa-cyclopropa[a]inden-1a-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-Phenyl-acrylic acid (1aS,1bS,2S,5aR,6S,6aS)-6-acetoxy-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1b,5a,6,6a-tetrahydro-2H-1,3-dioxa-cyclopropa[a]inden-1a-ylmethyl ester

There total 1 articles about (E)-3-Phenyl-acrylic acid (1aS,1bS,2S,5aR,6S,6aS)-6-acetoxy-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1b,5a,6,6a-tetrahydro-2H-1,3-dioxa-cyclopropa[a]inden-1a-ylmethyl 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:

acetic anhydride (108-24-7) + 10-O-trans-cinnamoylcatalpol (1399-49-1) → (E)-3-Phenyl-acrylic acid (1aS,1bS,2S,5aR,6S,6aS)-6-acetoxy-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1b,5a,6,6a-tetrahydro-2H-1,3-dioxa-cyclopropa[a]inden-1a-ylmethyl ester (31939-25-0)

Guidance literature:

With pyridine; for 2.5h; Yield given; Ambient temperature;

DOI:10.1002/(SICI)1099-0690(199802)1998:2<365::AID-EJOC365>3.0.CO;2-Z

Reference yield:

(E)-3-Phenyl-acrylic acid (1aS,1bS,2S,5aR,6S,6aS)-6-acetoxy-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1b,5a,6,6a-tetrahydro-2H-1,3-dioxa-cyclopropa[a]inden-1a-ylmethyl ester (31939-25-0) → C32H32O8

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / LiAlH₄ / tetrahydrofuran / reflux, 4 h, RT, overnight, reflux, 0.5 h

2: 81 percent / PPTS / acetone / 2.5 h / Ambient temperature

3: 1.) ozone; 2.) NaBH₄ / 1.) EtOH, MeOH, -78 deg C, 15 min; 2.) EtOH, MeOH, 5 deg C, 2 d

4: 91 percent / pyridine / CH₂Cl₂ / 16 h / 4 °C

With pyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; ozone; pyridinium p-toluenesulfonate; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1002/(SICI)1099-0690(199802)1998:2<365::AID-EJOC365>3.0.CO;2-Z

upstream raw materials:

acetic anhydride

10-O-trans-cinnamoylcatalpol