(1R,3Z,7S,9E,11S,15S,17R)-11-hydroxy-7-{(1S,2E)-1-(4-methoxybenzyloxy)-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]allyl}-15-methyl-13-methylene-6,21-dioxabicyclo[15.3.1]henicosa-3,9,19-trien-5-one

Base Information

Chemical Name:(1R,3Z,7S,9E,11S,15S,17R)-11-hydroxy-7-{(1S,2E)-1-(4-methoxybenzyloxy)-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]allyl}-15-methyl-13-methylene-6,21-dioxabicyclo[15.3.1]henicosa-3,9,19-trien-5-one
CAS No.:312695-96-8
Molecular Formula:C₃₈H₅₀O₇
Molecular Weight:618.811
Hs Code.:

(1R,3Z,7S,9E,11S,15S,17R)-11-hydroxy-7-{(1S,2E)-1-(4-methoxybenzyloxy)-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]allyl}-15-methyl-13-methylene-6,21-dioxabicyclo[15.3.1]henicosa-3,9,19-trien-5-one

Synonyms:(1R,3Z,7S,9E,11S,15S,17R)-11-hydroxy-7-{(1S,2E)-1-(4-methoxybenzyloxy)-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]allyl}-15-methyl-13-methylene-6,21-dioxabicyclo[15.3.1]henicosa-3,9,19-trien-5-one

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Chemical Property of (1R,3Z,7S,9E,11S,15S,17R)-11-hydroxy-7-{(1S,2E)-1-(4-methoxybenzyloxy)-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]allyl}-15-methyl-13-methylene-6,21-dioxabicyclo[15.3.1]henicosa-3,9,19-trien-5-one

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Technology Process of (1R,3Z,7S,9E,11S,15S,17R)-11-hydroxy-7-{(1S,2E)-1-(4-methoxybenzyloxy)-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]allyl}-15-methyl-13-methylene-6,21-dioxabicyclo[15.3.1]henicosa-3,9,19-trien-5-one

There total 33 articles about (1R,3Z,7S,9E,11S,15S,17R)-11-hydroxy-7-{(1S,2E)-1-(4-methoxybenzyloxy)-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]allyl}-15-methyl-13-methylene-6,21-dioxabicyclo[15.3.1]henicosa-3,9,19-trien-5-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: 97.0%

: 1198463-69-2
(1R,3Z,7S,9E,15S,17R)-7-{(S,E)-1-(4-methoxybenzyloxy)-3-[(S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]allyl}-15-methyl-13-methylene-6,21-dioxabicyclo[15.3.1]henicosa-3,9,19-triene-5,11-dione

: 312695-96-8
(1R,3Z,7S,9E,11S,15S,17R)-11-hydroxy-7-{(1S,2E)-1-(4-methoxybenzyloxy)-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]allyl}-15-methyl-13-methylene-6,21-dioxabicyclo[15.3.1]henicosa-3,9,19-trien-5-one

Guidance literature:: (1R,3Z,7S,9E,15S,17R)-7-{(S,E)-1-(4-methoxybenzyloxy)-3-[(S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]allyl}-15-methyl-13-methylene-6,21-dioxabicyclo[15.3.1]henicosa-3,9,19-triene-5,11-dione; With borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; at 0 ℃; Inert atmosphere;

With water; In tetrahydrofuran; toluene; at 0 - 20 ℃;
DOI:10.1021/ja907924j

Reference yield:

: 312695-87-7
(3Z,9E)-(1R,7S,11S,15S,17R)-7-[(E)-(S)-1-(4-Methoxy-benzyloxy)-3-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-allyl]-11-methoxymethoxy-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one

: 312695-96-8
(1R,3Z,7S,9E,11S,15S,17R)-11-hydroxy-7-{(1S,2E)-1-(4-methoxybenzyloxy)-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]allyl}-15-methyl-13-methylene-6,21-dioxabicyclo[15.3.1]henicosa-3,9,19-trien-5-one

Guidance literature:: With pyridinium p-toluenesulfonate; In tert-butyl alcohol; at 84 ℃; for 45h;
DOI:10.1021/ja0027416

Reference yield:

: (E)-(3S,4S)-6-Benzenesulfonyl-1-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-hex-1-ene-3,4-diol

: 312695-96-8
(1R,3Z,7S,9E,11S,15S,17R)-11-hydroxy-7-{(1S,2E)-1-(4-methoxybenzyloxy)-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]allyl}-15-methyl-13-methylene-6,21-dioxabicyclo[15.3.1]henicosa-3,9,19-trien-5-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: 71 percent / CSA / CH₂Cl₂ / 23 °C

2.1: 74 percent / Dibal-H / CH₂Cl₂ / -78 °C

3.1: n-BuLi / 0.25 h / -78 °C

3.2: 2 h / -78 - -40 °C

4.1: Et₃N; DMAP

5.1: Na(Hg); Na₂HPO₄ / methanol / 2.5 h / -20 - 23 °C

6.1: Cl₃C₆H₂COCl; i-Pr₂EtN; DMAP

7.1: 99 percent / aq. AcOH / tetrahydrofuran / 23 °C

8.1: 79 percent / NaIO₄ / CH₂Cl₂ / 23 °C

9.1: K₂CO₃; 18-C-6 / 3 h / -20 - 0 °C

10.1: PPTS / 2-methyl-propan-2-ol / 45 h / 84 °C

With dmap; sodium periodate; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; 18-crown-6 ether; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol; 5.1: Julia olefination / 9.1: Horner-Emmons reaction;
DOI:10.1021/ja0027416