(S)-2-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-1-((1S,2R,3S,4S,5R,6R)-5-((dimethyl(phenyl)silyl)methyl)-4-((4-methoxybenzyl)oxy)-2-vinyl-7-oxabicyclo[4.1.0]heptan-3-yl)but-3-en-1-one

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Chemical Name:(S)-2-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-1-((1S,2R,3S,4S,5R,6R)-5-((dimethyl(phenyl)silyl)methyl)-4-((4-methoxybenzyl)oxy)-2-vinyl-7-oxabicyclo[4.1.0]heptan-3-yl)but-3-en-1-one
CAS No.:1006380-44-4
Molecular Formula:C₄₇H₅₈O₅Si₂
Molecular Weight:759.146
Hs Code.:

(S)-2-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-1-((1S,2R,3S,4S,5R,6R)-5-((dimethyl(phenyl)silyl)methyl)-4-((4-methoxybenzyl)oxy)-2-vinyl-7-oxabicyclo[4.1.0]heptan-3-yl)but-3-en-1-one

Synonyms:(S)-2-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-1-((1S,2R,3S,4S,5R,6R)-5-((dimethyl(phenyl)silyl)methyl)-4-((4-methoxybenzyl)oxy)-2-vinyl-7-oxabicyclo[4.1.0]heptan-3-yl)but-3-en-1-one

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Chemical Property of (S)-2-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-1-((1S,2R,3S,4S,5R,6R)-5-((dimethyl(phenyl)silyl)methyl)-4-((4-methoxybenzyl)oxy)-2-vinyl-7-oxabicyclo[4.1.0]heptan-3-yl)but-3-en-1-one

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Technology Process of (S)-2-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-1-((1S,2R,3S,4S,5R,6R)-5-((dimethyl(phenyl)silyl)methyl)-4-((4-methoxybenzyl)oxy)-2-vinyl-7-oxabicyclo[4.1.0]heptan-3-yl)but-3-en-1-one

There total 18 articles about (S)-2-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-1-((1S,2R,3S,4S,5R,6R)-5-((dimethyl(phenyl)silyl)methyl)-4-((4-methoxybenzyl)oxy)-2-vinyl-7-oxabicyclo[4.1.0]heptan-3-yl)but-3-en-1-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: 85.0%

: 1006380-60-4
(S)-2-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-1-((1S,2S,5S,6S)-5-((dimethyl(phenyl)silyl)methyl)-6-((4-methoxybenzyl)oxy)-2-vinylcyclohex-3-en-1-yl)but-3-en-1-one

: 1006380-44-4
(S)-2-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-1-((1S,2R,3S,4S,5R,6R)-5-((dimethyl(phenyl)silyl)methyl)-4-((4-methoxybenzyl)oxy)-2-vinyl-7-oxabicyclo[4.1.0]heptan-3-yl)but-3-en-1-one

Guidance literature:: With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In chloroform; at -15 ℃; for 6h;
DOI:10.1021/ol7027338

Reference yield:

: 1006380-52-4
(1S,2S,5S,6S)-5-((dimethyl(phenyl)silyl)methyl)-6-((4-methoxybenzyl)oxy)-2-vinylcyclohex-3-enecarbaldehyde

: 1006380-44-4
(S)-2-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-1-((1S,2R,3S,4S,5R,6R)-5-((dimethyl(phenyl)silyl)methyl)-4-((4-methoxybenzyl)oxy)-2-vinyl-7-oxabicyclo[4.1.0]heptan-3-yl)but-3-en-1-one

Guidance literature:: Multi-step reaction with 3 steps

1: chromium dichloride / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

2: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.25 h / Inert atmosphere

3: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / -15 - 0 °C / Inert atmosphere

With chromium dichloride; sodium hydrogencarbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide; 1: Hiyama-Nozaki-Kishi reaction;
DOI:10.1002/chem.201200257

Reference yield:

: (1SR,2SR,5SR,6RS)-5,6-bis((benzyloxy)methyl)-2-((dimethyl(phenyl)silyl)methyl)cyclohex-3-enol

: 1006380-44-4
(S)-2-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-1-((1S,2R,3S,4S,5R,6R)-5-((dimethyl(phenyl)silyl)methyl)-4-((4-methoxybenzyl)oxy)-2-vinyl-7-oxabicyclo[4.1.0]heptan-3-yl)but-3-en-1-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: CHIRACEL OD column / hexane; isopropyl alcohol / Resolution of racemate; Inert atmosphere

2.1: naphthalene; lithium / tetrahydrofuran / 2 h / -20 °C / Inert atmosphere

3.1: camphor-10-sulfonic acid / benzene / 3 h / Inert atmosphere; Reflux

4.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.25 h / Inert atmosphere

5.1: cerium(III) chloride / tetrahydrofuran; pentane / 1.25 h / -78 °C / Inert atmosphere

5.2: -30 °C / Inert atmosphere

6.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide; toluene / 60 °C / Inert atmosphere

7.1: diisobutylaluminium hydride / dichloromethane; toluene / 4 h / 0 °C / Inert atmosphere

8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.5 h / Inert atmosphere

9.1: chromium dichloride / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

10.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.25 h / Inert atmosphere

11.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / -15 - 0 °C / Inert atmosphere

With chromium dichloride; cerium(III) chloride; naphthalene; camphor-10-sulfonic acid; sodium hexamethyldisilazane; lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene; pentane; benzene; 9.1: Hiyama-Nozaki-Kishi reaction;
DOI:10.1002/chem.201200257