(S)-1-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-yn-1-ol

Base Information

Chemical Name:(S)-1-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-yn-1-ol
CAS No.:143360-25-2
Molecular Formula:C₁₇H₂₂O₄
Molecular Weight:290.359
Hs Code.:

Synonyms:(S)-1-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-yn-1-ol

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Chemical Property of (S)-1-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-yn-1-ol

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Technology Process of (S)-1-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-yn-1-ol

There total 13 articles about (S)-1-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-yn-1-ol 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: 86.0%

: 81028-12-8
(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde

: 106-96-7
propargyl bromide

: 143360-25-2
(S)-1-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-yn-1-ol

Guidance literature:: propargyl bromide; With zinc; In diethyl ether; N,N-dimethyl-formamide;

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde; In diethyl ether; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(02)01815-4

Reference yield: 84.0%

: (4S,5S)-4-((benzyloxy)methyl)-2,2-dimethyl-5-((S)-oxiran-2-yl)-1,3-dioxolane

: 1216963-74-4
lithium acetylide-ethylenediamine complex

: 143360-25-2
(S)-1-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-yn-1-ol

Guidance literature:: In dimethyl sulfoxide; at 0 - 20 ℃; for 4h;
DOI:10.1016/j.tet.2015.06.035

Reference yield:

: 78469-77-9,81076-11-1,128820-40-6,78513-03-8
(4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane

: 143360-25-2
(S)-1-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-yn-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: oxalyl chloride; DMSO / CH₂Cl₂ / 0.5 h / -60 °C

1.2: 85 percent / triethylamine / CH₂Cl₂ / 2.5 h / -60 - 25 °C

2.1: 86 percent / zinc powder / diethyl ether; dimethylformamide / 10 h / 23 - 25 °C

With oxalyl dichloride; dimethyl sulfoxide; zinc; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1.1: Swern oxidation;
DOI:10.1021/jo0205208