(4S,5S)-5-benzyloxy-4-(2-trimethylsilylethynyl)-2,2-dimethyl-1,3-dioxane

Base Information

Chemical Name:(4S,5S)-5-benzyloxy-4-(2-trimethylsilylethynyl)-2,2-dimethyl-1,3-dioxane
CAS No.:161459-66-1
Molecular Formula:C₁₈H₂₆O₃Si
Molecular Weight:318.488
Hs Code.:

Synonyms:(4S,5S)-5-benzyloxy-4-(2-trimethylsilylethynyl)-2,2-dimethyl-1,3-dioxane

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Chemical Property of (4S,5S)-5-benzyloxy-4-(2-trimethylsilylethynyl)-2,2-dimethyl-1,3-dioxane

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Technology Process of (4S,5S)-5-benzyloxy-4-(2-trimethylsilylethynyl)-2,2-dimethyl-1,3-dioxane

There total 6 articles about (4S,5S)-5-benzyloxy-4-(2-trimethylsilylethynyl)-2,2-dimethyl-1,3-dioxane 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: 95.0%

: 77-76-9
2,2-dimethoxy-propane

: 169238-09-9
(2R,3R)-2-benzyloxy-5-trimethylsilylpent-4-yne-1,3-diol

: 161459-66-1
(4S,5S)-5-benzyloxy-4-(2-trimethylsilylethynyl)-2,2-dimethyl-1,3-dioxane

Guidance literature:: DOI:10.1016/0040-4039(94)88514-1

Reference yield:

: 2-(benzyloxy)-1-(trimethylsiloxy)-1-phenoxyethylene

: 161459-66-1
(4S,5S)-5-benzyloxy-4-(2-trimethylsilylethynyl)-2,2-dimethyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 3 steps

1: (R)-1-methyl-2-[(N-1-naphthylamino)methyl]pyrrolidine / SnO; Sn(OTf)2 / various solvent(s) / 5 h / -78 °C

2: 83 percent / diisobutylaluminum hydride / CH₂Cl₂; toluene / 0.83 h / -78 °C

3: p-TsOH / dimethylformamide / 10 h / 20 °C

With N-(((R)-1-methylpyrrolidin-2-yl)methyl)naphthalen-1-amine; diisobutylaluminium hydride; tin(II) trifluoromethanesulfonate; tin(II) oxide; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide; toluene; 1: Condensation / 2: Reduction / 3: Cyclization;
DOI:10.1016/S0040-4020(98)00484-0

Reference yield:

: 161459-65-0
phenyl (2S,3R)-2-benzyloxy-3-hydroxy-5-trimethylsilylpent-4-ynoate

: 161459-66-1
(4S,5S)-5-benzyloxy-4-(2-trimethylsilylethynyl)-2,2-dimethyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 2 steps

1: 83 percent / diisobutylaluminum hydride / CH₂Cl₂; toluene / 0.83 h / -78 °C

2: p-TsOH / dimethylformamide / 10 h / 20 °C

With diisobutylaluminium hydride; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide; toluene; 1: Reduction / 2: Cyclization;
DOI:10.1016/S0040-4020(98)00484-0