(3S)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-hydroxymethyl-5-trimethylsilanyl-pent-4-ynoic acid dimethylamide

Base Information

Chemical Name:(3S)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-hydroxymethyl-5-trimethylsilanyl-pent-4-ynoic acid dimethylamide
CAS No.:634912-00-8
Molecular Formula:C₃₀H₄₅NO₃Si₂
Molecular Weight:523.863
Hs Code.:

Synonyms:(3S)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-hydroxymethyl-5-trimethylsilanyl-pent-4-ynoic acid dimethylamide

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Chemical Property of (3S)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-hydroxymethyl-5-trimethylsilanyl-pent-4-ynoic acid dimethylamide

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Technology Process of (3S)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-hydroxymethyl-5-trimethylsilanyl-pent-4-ynoic acid dimethylamide

There total 4 articles about (3S)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-hydroxymethyl-5-trimethylsilanyl-pent-4-ynoic acid dimethylamide 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: 75.3%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 634911-87-8
(3S)-3-(3-hydroxy-propyl)-3-hydroxymethyl-5-trimethylsilanyl-pent-4-ynoic acid dimethylamide

: 634912-00-8
(3S)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-hydroxymethyl-5-trimethylsilanyl-pent-4-ynoic acid dimethylamide

Guidance literature:: With dmap; triethylamine; In dichloromethane; at -5 ℃; for 2.5h;
DOI:10.1016/j.tet.2003.09.005

Reference yield:

: 634911-85-6
(2S)-3-[(trimethyl-silanyl)-ethynyl]-cyclopent-2-enol

: 634912-00-8
(3S)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-hydroxymethyl-5-trimethylsilanyl-pent-4-ynoic acid dimethylamide

Guidance literature:: Multi-step reaction with 5 steps

1: 84 percent / xylene / 2 h / Heating

2: N-methylmorpholine N-oxide; osmium tetroxide / acetone; H₂O; 2-methyl-propan-2-ol / 1.5 h / 0 - 20 °C

3: sodium periodate / tetrahydrofuran; H₂O / 1 h / 0 °C

4: 5.47 g / sodium borohydride / ethanol / 0.33 h / 20 °C

5: 75.3 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2.5 h / -5 °C

With dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; xylene; tert-butyl alcohol; 1: Claisen-Eschenmoser rearrangement;
DOI:10.1016/j.tet.2003.09.005

Reference yield:

: 634911-86-7
(2R)-N,N-dimethyl-2-[1-[(trimethyl-silanyl)-ethynyl]-cyclopent-2-enyl]-acetamide

: 634912-00-8
(3S)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-hydroxymethyl-5-trimethylsilanyl-pent-4-ynoic acid dimethylamide

Guidance literature:: Multi-step reaction with 4 steps

1: N-methylmorpholine N-oxide; osmium tetroxide / acetone; H₂O; 2-methyl-propan-2-ol / 1.5 h / 0 - 20 °C

2: sodium periodate / tetrahydrofuran; H₂O / 1 h / 0 °C

3: 5.47 g / sodium borohydride / ethanol / 0.33 h / 20 °C

4: 75.3 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2.5 h / -5 °C

With dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; tert-butyl alcohol;
DOI:10.1016/j.tet.2003.09.005