O-benzyl (+/-)-iso-β-peltatine

Base Information

• Chemical Name: O-benzyl (+/-)-iso-β-peltatine
• CAS No.: 82299-45-4
• Molecular Formula: C₂₉H₂₈O₈
• Molecular Weight: 504.537
• Mol file: 82299-45-4.mol

Synonyms:O-benzyl (+/-)-iso-β-peltatine

Chemical Property of O-benzyl (+/-)-iso-β-peltatine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-benzyl (+/-)-iso-β-peltatine

There total 25 articles about O-benzyl (+/-)-iso-β-peltatine 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: 88.0%

(5aS,8aR)-10-Benzyloxy-5-hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one (82314-35-0) → (5aR,8aR)-10-Benzyloxy-5-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one (82299-45-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1016/S0040-4039(00)86991-9

Reference yield: 88.0%

(benzyloxy-2 methylenedioxy-3,4 benzyl)-4 <(trimethoxy-3,4,5-phenyl)hydroxymethyl>-3 dihydro-3H-furannone-2 (92830-78-9,92936-07-7) → O-benzyl (+/-)-iso-β-peltatine (82299-45-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 6h; Ambient temperature;

DOI:10.1016/S0040-4020(01)83505-5

Reference yield:

2H-benzo[d]1,3-dioxolane-4-carbaldehyde (7797-83-3) → O-benzyl (+/-)-iso-β-peltatine (82299-45-4)

Guidance literature:

Multi-step reaction with 11 steps

1: m-chloroperbenzoic acid / CH₂Cl₂ / 36 h / Heating

2: 10percent KOH / methanol / 1.5 h / Ambient temperature

3: 98 percent / trifluoroacetate d argent, brome / CHCl₃ / 0.5 h / Ambient temperature

4: 1.) 1.6M n-BuLi / 1.) hexane, ether, reflux, 1.75 h; 2.) reflux, 45 min

5: 97 percent / K₂CO₃, NaI / ethanol / 16 h / Heating

6: 75 percent / NaOMe / methanol / 6 h / Heating

7: 1.) 2N KOH; 2.) CaCl₂, NaBH₄, 2.5M KOH / 1.) water; 2.) ethanol, 50 deg C, 1 h

8: 86 percent / H₂ / 5percent Pd/C / ethyl acetate / 18 h / 3800 Torr / Ambient temperature

9: 84 percent / K₂CO₃, NaI / acetone / 16 h / Heating

10: 71.25 percent / hexamethyldisilylamine, 1.6M n-BuLi / hexane; benzene / 0.05 h / 5 - 10 °C

11: 88 percent / trifluoroacetic acid / CH₂Cl₂ / 6 h / Ambient temperature

With potassium hydroxide; sodium tetrahydroborate; n-butyllithium; trifluoroacetate d argent; hydrogen; bromine; sodium methylate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; sodium iodide; calcium chloride; palladium on activated charcoal; In methanol; ethanol; hexane; dichloromethane; chloroform; ethyl acetate; acetone; benzene;

DOI:10.1016/S0040-4020(01)83505-5

upstream raw materials:

(5aS,8aR)-10-Benzyloxy-5-hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

2H-benzo[d]1,3-dioxolane-4-carbaldehyde

benzyloxy-2 piperonal

2,3-dihydroxybenzaldehyde

Downstream raw materials:

(+/-)-iso β-peltatine

(+/-)-iso-β-peltatine

Refernces

• 1、 Brown, Eric,Loriot, Michel,Robin, Jean-Pierre. "SYNTHESE TOTALES DE LA (+/-) ISO β-PELTATINE ET DE SES ANALOGUES". . p. 949 - 952. Retrieved 2007/10/02.