(7E,9E)-(2S,3aR,5R,6R,11R,12R,16R,17S,17aS)-12-Ethyl-6,16-dihydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-2,3,3a,4,5,6,11,12,15,16,17,17a-dodecahydro-1,13-dioxa-cyclopentacyclohexadecen-14-one

Base Information

Chemical Name:(7E,9E)-(2S,3aR,5R,6R,11R,12R,16R,17S,17aS)-12-Ethyl-6,16-dihydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-2,3,3a,4,5,6,11,12,15,16,17,17a-dodecahydro-1,13-dioxa-cyclopentacyclohexadecen-14-one
CAS No.:81114-73-0
Molecular Formula:C₄₃H₅₄O₇
Molecular Weight:682.898
Hs Code.:

(7E,9E)-(2S,3aR,5R,6R,11R,12R,16R,17S,17aS)-12-Ethyl-6,16-dihydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-2,3,3a,4,5,6,11,12,15,16,17,17a-dodecahydro-1,13-dioxa-cyclopentacyclohexadecen-14-one

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Chemical Property of (7E,9E)-(2S,3aR,5R,6R,11R,12R,16R,17S,17aS)-12-Ethyl-6,16-dihydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-2,3,3a,4,5,6,11,12,15,16,17,17a-dodecahydro-1,13-dioxa-cyclopentacyclohexadecen-14-one

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Technology Process of (7E,9E)-(2S,3aR,5R,6R,11R,12R,16R,17S,17aS)-12-Ethyl-6,16-dihydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-2,3,3a,4,5,6,11,12,15,16,17,17a-dodecahydro-1,13-dioxa-cyclopentacyclohexadecen-14-one

There total 42 articles about (7E,9E)-(2S,3aR,5R,6R,11R,12R,16R,17S,17aS)-12-Ethyl-6,16-dihydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-2,3,3a,4,5,6,11,12,15,16,17,17a-dodecahydro-1,13-dioxa-cyclopentacyclohexadecen-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:

: 81132-63-0
20-O-Methyl-23-O-trityltylonolide Hemiacetal

: 81114-73-0,81132-62-9,81600-33-1,81600-34-2,84710-26-9
(7E,9E)-(2S,3aR,5R,6R,11R,12R,16R,17S,17aS)-12-Ethyl-6,16-dihydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-2,3,3a,4,5,6,11,12,15,16,17,17a-dodecahydro-1,13-dioxa-cyclopentacyclohexadecen-14-one

: 84710-26-9
(7E,9E)-(2S,3aR,5R,6S,11R,12R,16R,17S,17aS)-12-Ethyl-6,16-dihydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-2,3,3a,4,5,6,11,12,15,16,17,17a-dodecahydro-1,13-dioxa-cyclopentacyclohexadecen-14-one

Guidance literature:: With sodium tetrahydroborate; In methanol; at -20 ℃; Yield given. Yields of byproduct given; room temp.;
DOI:10.1021/jo00154a033

Reference yield:

: 81114-52-5,81132-63-0,84171-61-9
(7E,9E)-(3aR,5R,11R,12R,16R,17S,17aS)-12-Ethyl-16-hydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-3,3a,4,5,11,12,15,16,17,17a-decahydro-2H-1,13-dioxa-cyclopentacyclohexadecene-6,14-dione

: 81114-73-0,81132-62-9,81600-33-1,81600-34-2,84710-26-9
(7E,9E)-(3aR,5R,11R,12R,16R,17S,17aS)-12-Ethyl-6,16-dihydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-2,3,3a,4,5,6,11,12,15,16,17,17a-dodecahydro-1,13-dioxa-cyclopentacyclohexadecen-14-one

Guidance literature:: With sodium tetrahydroborate; In methanol; at 20 ℃;
DOI:10.1016/S0040-4039(01)82047-5

Reference yield:

: 78785-21-4
3,5-Didesoxy-1,2-O-isopropyliden-3-C-methyl-α-D-xylo-hexofuranose

: 81114-73-0,81132-62-9,81600-33-1,81600-34-2,84710-26-9
(7E,9E)-(3aR,5R,11R,12R,16R,17S,17aS)-12-Ethyl-6,16-dihydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-2,3,3a,4,5,6,11,12,15,16,17,17a-dodecahydro-1,13-dioxa-cyclopentacyclohexadecen-14-one

Guidance literature:: Multi-step reaction with 19 steps

1: NaH / dimethylformamide / 1 h / 20 °C

2: H₂O, H₂SO₄ / 2-methyl-propan-2-ol / 50 °C

3: toluene / 18 h / 50 °C

4: TsOH / dimethylformamide / 1 h / 20 °C

5: BuLi / 2.5 h / -78 °C

6: BF₃ - Et₂O / 18 h / 20 °C

7: DIBAL / toluene / 0.5 h / -78 °C

8: Amberlyst 15 (H type) / 2 h / 20 °C

9: NaH / dimethylformamide / 4 h / 20 °C

10: 85 percent / CdCO₃, HgCl₂ / acetone; H₂O / 1 h / 20 °C

11: 90 percent / toluene / 90 h / 60 °C

12: H₂ / Pd-black / methanol / 20 °C / 2280 Torr

13: O₂ / Pt-black, NaHCO₃ / H₂O / 80 °C

14: 52 percent / diethyl ether / 20 °C

15: 41 percent / LDA / tetrahydrofuran / 2 h / -78 - 0 °C

16: NaBH₄ / methanol / 0 °C

17: 85 percent / H₂O, KOH / methanol / 15 h / 60 °C

18: Ph₃P / 20 °C

19: toluene / 20 h / 110 °C

With potassium hydroxide; sodium tetrahydroborate; n-butyllithium; cadmium(II) carbonate; Amberlyst 15 (H type); sulfuric acid; boron trifluoride diethyl etherate; water; hydrogen; oxygen; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triphenylphosphine; mercury dichloride; lithium diisopropyl amide; sodium hydrogencarbonate; palladium; platinum; In tetrahydrofuran; methanol; diethyl ether; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;
DOI:10.1016/S0040-4039(01)82047-5