1-[Benzyl(trimethylsilylmethyl)amino]-1,4,5-trideoxy-2,3-O-(1-methylethylidene)-D-threo-pent-4-ynitol

Base Information

Chemical Name:1-[Benzyl(trimethylsilylmethyl)amino]-1,4,5-trideoxy-2,3-O-(1-methylethylidene)-D-threo-pent-4-ynitol
CAS No.:319924-32-8
Molecular Formula:C₁₉H₂₉NO₂Si
Molecular Weight:331.53
Hs Code.:

Synonyms:1-[Benzyl(trimethylsilylmethyl)amino]-1,4,5-trideoxy-2,3-O-(1-methylethylidene)-D-threo-pent-4-ynitol

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Chemical Property of 1-[Benzyl(trimethylsilylmethyl)amino]-1,4,5-trideoxy-2,3-O-(1-methylethylidene)-D-threo-pent-4-ynitol

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Technology Process of 1-[Benzyl(trimethylsilylmethyl)amino]-1,4,5-trideoxy-2,3-O-(1-methylethylidene)-D-threo-pent-4-ynitol

There total 7 articles about 1-[Benzyl(trimethylsilylmethyl)amino]-1,4,5-trideoxy-2,3-O-(1-methylethylidene)-D-threo-pent-4-ynitol 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: 65.0%

: 53215-95-5
N-(trimethylsilylmethyl)benzylamine

: 319924-31-7
(4S,5R)-4-(Bromomethyl)-5-ethynyl-2,2-dimethyl-1,3-dioxolane

: 319924-32-8
1-[Benzyl(trimethylsilylmethyl)amino]-1,4,5-trideoxy-2,3-O-(1-methylethylidene)-D-threo-pent-4-ynitol

Guidance literature:: With potassium carbonate; In acetonitrile; for 96h; Heating;
DOI:10.1016/S0040-4039(00)01553-7

Reference yield:

: 125993-65-9
(4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

: 319924-32-8
1-[Benzyl(trimethylsilylmethyl)amino]-1,4,5-trideoxy-2,3-O-(1-methylethylidene)-D-threo-pent-4-ynitol

Guidance literature:: Multi-step reaction with 5 steps

1: 65 percent / Ph₃P / CH₂Cl₂ / 2 h / 0 °C

2: 90 percent / BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

3: 85 percent / TBAF / tetrahydrofuran / 4 h / 0 - 20 °C

4: 660 mg / CBr₄; Ph₃P / CH₂Cl₂ / 1 h / 0 - 20 °C

5: 65 percent / K₂CO₃; TBAI / acetonitrile / 96 h / Heating

With n-butyllithium; carbon tetrabromide; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; potassium carbonate; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; acetonitrile;
DOI:10.1055/s-2001-15063

Reference yield:

: 320396-46-1
1,2-Dideoxy-3,4-O-(1-methylethylidene)-D-threo-pent-1-ynitol

: 319924-32-8
1-[Benzyl(trimethylsilylmethyl)amino]-1,4,5-trideoxy-2,3-O-(1-methylethylidene)-D-threo-pent-4-ynitol

Guidance literature:: Multi-step reaction with 2 steps

1: 660 mg / CBr₄; Ph₃P / CH₂Cl₂ / 1 h / 0 - 20 °C

2: 65 percent / K₂CO₃; TBAI / acetonitrile / 96 h / Heating

With carbon tetrabromide; tetra-(n-butyl)ammonium iodide; potassium carbonate; triphenylphosphine; In dichloromethane; acetonitrile;
DOI:10.1055/s-2001-15063