(S)-[(2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-(tert-Butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-acetyl azide

Base Information

Chemical Name:(S)-[(2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-(tert-Butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-acetyl azide
CAS No.:1054610-92-2
Molecular Formula:C₃₈H₅₃N₃O₇Si
Molecular Weight:691.94
Hs Code.:

(S)-[(2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-(tert-Butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-acetyl azide

Synonyms:(S)-[(2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-(tert-Butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-acetyl azide

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Chemical Property of (S)-[(2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-(tert-Butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-acetyl azide

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Technology Process of (S)-[(2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-(tert-Butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-acetyl azide

There total 34 articles about (S)-[(2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-(tert-Butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-acetyl azide 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:

: 389123-18-6
(S)-[(2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-(tert-Butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-acetic acid

: 1054610-92-2
(S)-[(2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-(tert-Butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-acetyl azide

Guidance literature:: (S)-[(2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-(tert-Butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-acetic acid; With N-ethyl-N,N-diisopropylamine; isobutyl chloroformate; In acetone; at 0 ℃; for 0.5h;

With sodium azide; In acetone; at 0 ℃; for 1.5h; Further stages.;
DOI:10.1021/ja020635t

Reference yield:

: C₄₃H₆₂O₁₀Si

: 1054610-92-2
(S)-[(2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-(tert-Butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-acetyl azide

Guidance literature:: With sodium azide; In water; at 0 ℃; for 1.5h;
DOI:10.1021/ja012220y

Reference yield:

: 152386-85-1
(1R,2S)-1-((R)-2,2-diethyl-1,3-dioxolan-4-yl)-2-((4-methoxybenzyl)oxy)ethan-1-ol

: 1054610-92-2
(S)-[(2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-(tert-Butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-acetyl azide

Guidance literature:: Multi-step reaction with 12 steps

1.1: NaH / tetrahydrofuran

2.1: H₂SO₄ / methanol

3.1: PPh₃; DEAD / benzene / 0 °C

3.2: 150 °C / 1 Torr

4.1: t-BuLi / diethyl ether; pentane / -78 - -45 °C

4.2: 2-thienylcyanocuprate / diethyl ether; tetrahydrofuran; pentane / -78 - 45 °C

4.3: 77 percent / diethyl ether; tetrahydrofuran; pentane / 1.75 h / -45 - 0 °C

5.1: 94 percent / DCC; DMAP / CH₂Cl₂ / 0.5 h / 20 °C

6.1: 72 percent / HF*pyridine / tetrahydrofuran / 4.5 h / 20 °C

7.1: 92 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

8.1: 72 percent / NaHMDS / tetrahydrofuran / -78 - 0 °C

9.1: 59 percent / DDQ; H₂O / CH₂Cl₂ / 0.5 h / 0 °C

10.1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1.17 h / 20 °C

11.1: 20.6 mg / NaClO₂; sodium dihydrogenphosphate monohydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 1 h / 20 °C

12.1: N,N-diisopropylethylamine; i-BuOCOCl / acetone / 0.5 h / 0 °C

12.2: aq. NaN₃ / acetone / 1.5 h / 0 °C

With pyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; sulfuric acid; water; tert.-butyl lithium; sodium hexamethyldisilazane; sodium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; isobutyl chloroformate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone; tert-butyl alcohol; pentane; benzene; 5.1: Mitsunobu reaction / 8.1: Horner-Wadsworth-Emmoms macrocyclization;
DOI:10.1021/ja020635t