(2R,1'S,3S,4S)-Nα-Boc-O-tert-butyldimethylsilyl-3,4-(dibenzylaminomethano)prolinol

Base Information

Chemical Name:(2R,1'S,3S,4S)-Nα-Boc-O-tert-butyldimethylsilyl-3,4-(dibenzylaminomethano)prolinol
CAS No.:916763-87-6
Molecular Formula:C₃₁H₄₆N₂O₃Si
Molecular Weight:522.803
Hs Code.:

Synonyms:(2R,1'S,3S,4S)-Nα-Boc-O-tert-butyldimethylsilyl-3,4-(dibenzylaminomethano)prolinol

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Chemical Property of (2R,1'S,3S,4S)-Nα-Boc-O-tert-butyldimethylsilyl-3,4-(dibenzylaminomethano)prolinol

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Technology Process of (2R,1'S,3S,4S)-Nα-Boc-O-tert-butyldimethylsilyl-3,4-(dibenzylaminomethano)prolinol

There total 5 articles about (2R,1'S,3S,4S)-Nα-Boc-O-tert-butyldimethylsilyl-3,4-(dibenzylaminomethano)prolinol 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: 69.0%

: 5464-77-7
N,N-dibenzylformamide

: 220652-49-3
(R)-N-Boc-O-tertbutyldimethylsilyl-3,4-dehydroprolinol

: 916763-87-6
(2R,1'S,3S,4S)-Nα-Boc-O-tert-butyldimethylsilyl-3,4-(dibenzylaminomethano)prolinol

Guidance literature:: With methyltriisopropoxytitanium(IV); cyclohexylmagnesium bromide; In tetrahydrofuran; diethyl ether; for 19h;
DOI:10.1002/ejoc.200600404

Reference yield:

: 916763-86-5
(R)-N-allyl-N-Boc-O-(tert-butyldimethylsilyl)vinylglycinol

: 916763-87-6
(2R,1'S,3S,4S)-Nα-Boc-O-tert-butyldimethylsilyl-3,4-(dibenzylaminomethano)prolinol

Guidance literature:: Multi-step reaction with 2 steps

1: 72 percent / Grubbs I catalyst / CH₂Cl₂ / 17 h

2: 69 percent / cyclohexylmagnesium bromide; MeTi(OiPr)3 / diethyl ether; tetrahydrofuran / 19 h

With methyltriisopropoxytitanium(IV); cyclohexylmagnesium bromide; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1002/ejoc.200600404

Reference yield:

: 89985-86-4
(R)-2-(N-tert-butoxycarbonylamino)-3-buten-1-ol

: 916763-87-6
(2R,1'S,3S,4S)-Nα-Boc-O-tert-butyldimethylsilyl-3,4-(dibenzylaminomethano)prolinol

Guidance literature:: Multi-step reaction with 4 steps

1: imidazole / dimethylformamide / 2.5 h

2: 21.7 g / KOtBu / dimethylformamide / 0.25 h / -20 °C

3: 72 percent / Grubbs I catalyst / CH₂Cl₂ / 17 h

4: 69 percent / cyclohexylmagnesium bromide; MeTi(OiPr)3 / diethyl ether; tetrahydrofuran / 19 h

With 1H-imidazole; methyltriisopropoxytitanium(IV); potassium tert-butylate; cyclohexylmagnesium bromide; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200600404