(S,E)-methyl 5-(((benzyloxy)carbonyl)((tert-butyldimethylsilyl)oxy)amino)-7-(2-methyl-1,3-dioxolan-2-yl)hept-2-enoate

Base Information

Chemical Name:(S,E)-methyl 5-(((benzyloxy)carbonyl)((tert-butyldimethylsilyl)oxy)amino)-7-(2-methyl-1,3-dioxolan-2-yl)hept-2-enoate
CAS No.:1374584-68-5
Molecular Formula:C₂₆H₄₁NO₇Si
Molecular Weight:507.7
Hs Code.:

Synonyms:(S,E)-methyl 5-(((benzyloxy)carbonyl)((tert-butyldimethylsilyl)oxy)amino)-7-(2-methyl-1,3-dioxolan-2-yl)hept-2-enoate

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Chemical Property of (S,E)-methyl 5-(((benzyloxy)carbonyl)((tert-butyldimethylsilyl)oxy)amino)-7-(2-methyl-1,3-dioxolan-2-yl)hept-2-enoate

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Technology Process of (S,E)-methyl 5-(((benzyloxy)carbonyl)((tert-butyldimethylsilyl)oxy)amino)-7-(2-methyl-1,3-dioxolan-2-yl)hept-2-enoate

There total 10 articles about (S,E)-methyl 5-(((benzyloxy)carbonyl)((tert-butyldimethylsilyl)oxy)amino)-7-(2-methyl-1,3-dioxolan-2-yl)hept-2-enoate 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:

: 29021-98-5
3-(2-methyl-[1,3]dioxolan-2-yl)-propan-1-ol

: 1374584-68-5
(S,E)-methyl 5-(((benzyloxy)carbonyl)((tert-butyldimethylsilyl)oxy)amino)-7-(2-methyl-1,3-dioxolan-2-yl)hept-2-enoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C / Inert atmosphere

1.2: 1.25 h / -78 - 20 °C / Inert atmosphere

2.1: dichloromethane / 17 h / 20 °C

3.1: diisobutylaluminium hydride / hexane; dichloromethane / 2 h / -78 °C / Inert atmosphere

4.1: manganese(IV) oxide / dichloromethane / 24 h

5.1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine / chloroform / 41 h / 4 °C

6.1: chloroform / 2 h / 20 °C

With manganese(IV) oxide; oxalyl dichloride; (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; diisobutylaluminium hydride; dimethyl sulfoxide; In hexane; dichloromethane; chloroform; 2.1: Wittig reaction / 5.1: Michael condensation / 6.1: Wittig reaction;
DOI:10.1002/adsc.201100917

Reference yield:

: 1386999-48-9
(E)-methyl 5-(2-methyl-1,3-dioxolan-2-yl)pent-2-enoate

: 1374584-68-5
(S,E)-methyl 5-(((benzyloxy)carbonyl)((tert-butyldimethylsilyl)oxy)amino)-7-(2-methyl-1,3-dioxolan-2-yl)hept-2-enoate

Guidance literature:: Multi-step reaction with 4 steps

1: diisobutylaluminium hydride / hexane; dichloromethane / 2 h / -78 °C / Inert atmosphere

2: manganese(IV) oxide / dichloromethane / 24 h

3: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine / chloroform / 41 h / 4 °C

4: chloroform / 2 h / 20 °C

With manganese(IV) oxide; (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; diisobutylaluminium hydride; In hexane; dichloromethane; chloroform; 3: Michael condensation / 4: Wittig reaction;
DOI:10.1002/adsc.201100917

Reference yield:

: 930573-19-6
(E)-5-(2-methyl-1,3-dioxolan-2-yl)pent-2-enal

: 1374584-68-5
(S,E)-methyl 5-(((benzyloxy)carbonyl)((tert-butyldimethylsilyl)oxy)amino)-7-(2-methyl-1,3-dioxolan-2-yl)hept-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine / chloroform / 41 h / 4 °C

2: chloroform / 2 h / 20 °C

With (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; In chloroform; 1: Michael condensation / 2: Wittig reaction;
DOI:10.1002/adsc.201100917