(2S,3R,4E,6E,8S,9S)-1-O-(tert-butoxycarbamoyl)-3-hydroxy-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoate

Base Information

Chemical Name:(2S,3R,4E,6E,8S,9S)-1-O-(tert-butoxycarbamoyl)-3-hydroxy-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoate
CAS No.:298202-10-5
Molecular Formula:C₂₅H₃₇NO₆
Molecular Weight:447.572
Hs Code.:

Synonyms:(2S,3R,4E,6E,8S,9S)-1-O-(tert-butoxycarbamoyl)-3-hydroxy-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoate

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Chemical Property of (2S,3R,4E,6E,8S,9S)-1-O-(tert-butoxycarbamoyl)-3-hydroxy-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoate

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Technology Process of (2S,3R,4E,6E,8S,9S)-1-O-(tert-butoxycarbamoyl)-3-hydroxy-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoate

There total 12 articles about (2S,3R,4E,6E,8S,9S)-1-O-(tert-butoxycarbamoyl)-3-hydroxy-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoate 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: 96.0%

: 36016-38-3
tert-Butyl N-hydroxycarbamate

: 298202-09-2
(2'S,3'R,4'E,6'E,8'S,9'S,4S)-4-benzyl-3-[3'-hydroxy-9'-methoxy-2',6',8'-trimethyl-10'-phenyl-4,6-decadienoyl]-oxazolin-2-one

: 298202-10-5
(2S,3R,4E,6E,8S,9S)-1-O-(tert-butoxycarbamoyl)-3-hydroxy-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoate

Guidance literature:: With sodium hydride; In tetrahydrofuran; at -25 - 0 ℃;
DOI:10.1021/ol006347o

Reference yield:

: 36016-38-3
tert-Butyl N-hydroxycarbamate

: 1217320-30-3
C₃₀H₃₇NO₃S₂

: 298202-10-5
(2S,3R,4E,6E,8S,9S)-1-O-(tert-butoxycarbamoyl)-3-hydroxy-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoate

Guidance literature:: With 1H-imidazole; In tetrahydrofuran; at 20 ℃; for 12h;
DOI:10.1039/b920193a

Reference yield:

: 126399-05-1
(2E,4S,5S)-5-methoxy-2,4-dimethyl-6-phenylhex-2-en-1-ol

: 298202-10-5
(2S,3R,4E,6E,8S,9S)-1-O-(tert-butoxycarbamoyl)-3-hydroxy-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 99 percent / MnO₂ / CH₂Cl₂ / 24 h / -15 °C

2.1: 96 percent / toluene / 2.5 h / Heating

3.1: 99 percent / DIBAL-H / tetrahydrofuran / 2 h / -78 °C

4.1: 96 percent / MnO₂ / CH₂Cl₂ / 24 h / -15 °C

5.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 1.08 h / 0 - 3 °C

5.2: 91 percent / CH₂Cl₂ / -78 - 0 °C

6.1: 96 percent / NaH / tetrahydrofuran; various solvent(s) / -25 - 0 °C

With manganese(IV) oxide; di-n-butylboryl trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane; toluene; 1.1: Oxidation / 2.1: Wittig reaction / 3.1: Reduction / 4.1: Oxidation / 5.1: Substitution / 5.2: Evans aldol reaction / 6.1: Ring cleavage;
DOI:10.1021/ol006347o