(1R,3S,7S,9S,10S,12S,15Z,18R)-10-hydroxy-12-{(1S,2E)-1-[(4-methoxybenzyl)oxy]-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]allyl}-3-methyl-5-methylene-8,13,22-trioxatricyclo[16.3.1.0(7,9)]docosa-15,19-dien-14-one

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Chemical Name:(1R,3S,7S,9S,10S,12S,15Z,18R)-10-hydroxy-12-{(1S,2E)-1-[(4-methoxybenzyl)oxy]-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]allyl}-3-methyl-5-methylene-8,13,22-trioxatricyclo[16.3.1.0(7,9)]docosa-15,19-dien-14-one
CAS No.:1198463-56-7
Molecular Formula:C₃₈H₅₀O₈
Molecular Weight:634.81
Hs Code.:

(1R,3S,7S,9S,10S,12S,15Z,18R)-10-hydroxy-12-{(1S,2E)-1-[(4-methoxybenzyl)oxy]-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]allyl}-3-methyl-5-methylene-8,13,22-trioxatricyclo[16.3.1.0(7,9)]docosa-15,19-dien-14-one

Synonyms:(1R,3S,7S,9S,10S,12S,15Z,18R)-10-hydroxy-12-{(1S,2E)-1-[(4-methoxybenzyl)oxy]-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]allyl}-3-methyl-5-methylene-8,13,22-trioxatricyclo[16.3.1.0(7,9)]docosa-15,19-dien-14-one

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Chemical Property of (1R,3S,7S,9S,10S,12S,15Z,18R)-10-hydroxy-12-{(1S,2E)-1-[(4-methoxybenzyl)oxy]-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]allyl}-3-methyl-5-methylene-8,13,22-trioxatricyclo[16.3.1.0(7,9)]docosa-15,19-dien-14-one

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Technology Process of (1R,3S,7S,9S,10S,12S,15Z,18R)-10-hydroxy-12-{(1S,2E)-1-[(4-methoxybenzyl)oxy]-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]allyl}-3-methyl-5-methylene-8,13,22-trioxatricyclo[16.3.1.0(7,9)]docosa-15,19-dien-14-one

There total 2 articles about (1R,3S,7S,9S,10S,12S,15Z,18R)-10-hydroxy-12-{(1S,2E)-1-[(4-methoxybenzyl)oxy]-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]allyl}-3-methyl-5-methylene-8,13,22-trioxatricyclo[16.3.1.0(7,9)]docosa-15,19-dien-14-one 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: 86.0%

: 1198463-36-3
(1R,3Z,7S,9S,10E,15S,17R)-7-{(1S,2E)-1-(4-methoxybenzyloxy)-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]allyl}-9-hydroxy-15-methyl-13-methylene-6,21-dioxabicyclo[15.3.1]henicosa-3,10,19-trien-5-one

: 1198463-56-7
(1R,3S,7S,9S,10S,12S,15Z,18R)-10-hydroxy-12-{(1S,2E)-1-[(4-methoxybenzyl)oxy]-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]allyl}-3-methyl-5-methylene-8,13,22-trioxatricyclo[16.3.1.0(7,9)]docosa-15,19-dien-14-one

Guidance literature:: With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; In dodecane; dichloromethane; at -20 ℃; diastereoselective reaction; Inert atmosphere; Molecular sieve;
DOI:10.1021/ja907924j

Reference yield:

: 1198463-55-6
(1R,3Z,7S,9S,10E,15S,17R)-7-{(1S,2E)-1-(4-methoxybenzyloxy)-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]allyl}-9-(methoxymethoxy)-15-methyl-13-methylene-6,21-dioxabicyclo[15.3.1]henicosa-3,10,19-trien-5-one

: 1198463-56-7
(1R,3S,7S,9S,10S,12S,15Z,18R)-10-hydroxy-12-{(1S,2E)-1-[(4-methoxybenzyl)oxy]-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]allyl}-3-methyl-5-methylene-8,13,22-trioxatricyclo[16.3.1.0(7,9)]docosa-15,19-dien-14-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: pyridinium p-toluenesulfonate / tert-butyl alcohol / 8 h / 85 °C / Inert atmosphere

2.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate / dodecane; dichloromethane / 1 h / -20 °C / Molecular sieve; Inert atmosphere

2.2: 1 h / 0 °C / Molecular sieve; Inert atmosphere

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; pyridinium p-toluenesulfonate; In dodecane; dichloromethane; tert-butyl alcohol; 2.1: Sharpless epoxidation;
DOI:10.1002/chem.201102899