tert-butyl-(1S,2S)-N-[2-hydroxy-1-(hydroxymethyl)-3-phenylacetylenyl]carbamate

Base Information

Chemical Name:tert-butyl-(1S,2S)-N-[2-hydroxy-1-(hydroxymethyl)-3-phenylacetylenyl]carbamate
CAS No.:241478-38-6
Molecular Formula:C₁₆H₂₁NO₄
Molecular Weight:291.347
Hs Code.:

Synonyms:tert-butyl-(1S,2S)-N-[2-hydroxy-1-(hydroxymethyl)-3-phenylacetylenyl]carbamate

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Chemical Property of tert-butyl-(1S,2S)-N-[2-hydroxy-1-(hydroxymethyl)-3-phenylacetylenyl]carbamate

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Technology Process of tert-butyl-(1S,2S)-N-[2-hydroxy-1-(hydroxymethyl)-3-phenylacetylenyl]carbamate

There total 7 articles about tert-butyl-(1S,2S)-N-[2-hydroxy-1-(hydroxymethyl)-3-phenylacetylenyl]carbamate 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: 60.0%

: 241478-34-2
tert-butyl (4S)-4-<(1S)-1-hydroxy-3-phenyl-2-propynyl>-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

: 241478-38-6
tert-butyl-(1S,2S)-N-[2-hydroxy-1-(hydroxymethyl)-3-phenylacetylenyl]carbamate

Guidance literature:: With methanol; toluene-4-sulfonic acid; at 20 ℃;
DOI:10.1016/S0960-894X(99)00554-5

Reference yield:

: 102308-32-7
(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 241478-38-6
tert-butyl-(1S,2S)-N-[2-hydroxy-1-(hydroxymethyl)-3-phenylacetylenyl]carbamate

Guidance literature:: Multi-step reaction with 2 steps

1: 69 percent / n-BuLi; ZnBr₂ / diethyl ether / -78 - 20 °C

2: 60 percent / TosOH; MeOH / 20 °C

With methanol; n-butyllithium; toluene-4-sulfonic acid; zinc dibromide; In diethyl ether; 1: Addition / 2: Ring cleavage;
DOI:10.1016/S0960-894X(99)00554-5

Reference yield:

: 4440-01-1
lithium phenylacetylide

: 241478-38-6
tert-butyl-(1S,2S)-N-[2-hydroxy-1-(hydroxymethyl)-3-phenylacetylenyl]carbamate

Guidance literature:: Multi-step reaction with 2 steps

1: HMPA / tetrahydrofuran / 5 h / -78 °C

2: 53 percent / MeOH, Amberlyst 15 / 48 h / Ambient temperature

With methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; Amberlyst 15; In tetrahydrofuran;
DOI:10.1021/jm990091e