3-(benzyloxy)propyl 2,3,4,6-tetrakis-O-[tert-butyl(dimethyl)silyl]-α-D-mannopyranoside

Base Information

Chemical Name:3-(benzyloxy)propyl 2,3,4,6-tetrakis-O-[tert-butyl(dimethyl)silyl]-α-D-mannopyranoside
CAS No.:948297-89-0
Molecular Formula:C₄₀H₈₀O₇Si₄
Molecular Weight:785.413
Hs Code.:

Synonyms:3-(benzyloxy)propyl 2,3,4,6-tetrakis-O-[tert-butyl(dimethyl)silyl]-α-D-mannopyranoside

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Chemical Property of 3-(benzyloxy)propyl 2,3,4,6-tetrakis-O-[tert-butyl(dimethyl)silyl]-α-D-mannopyranoside

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Technology Process of 3-(benzyloxy)propyl 2,3,4,6-tetrakis-O-[tert-butyl(dimethyl)silyl]-α-D-mannopyranoside

There total 6 articles about 3-(benzyloxy)propyl 2,3,4,6-tetrakis-O-[tert-butyl(dimethyl)silyl]-α-D-mannopyranoside 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: 79.0%

: 948297-88-9
3-hydroxypropyl 2,3,4,6-tetrakis-O-[tert-butyl(dimethyl)silyl]-α-D-mannopyranoside

: 100-39-0
benzyl bromide

: 948297-89-0
3-(benzyloxy)propyl 2,3,4,6-tetrakis-O-[tert-butyl(dimethyl)silyl]-α-D-mannopyranoside

Guidance literature:: 3-hydroxypropyl 2,3,4,6-tetrakis-O-[tert-butyl(dimethyl)silyl]-α-D-mannopyranoside; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃;

benzyl bromide; In N,N-dimethyl-formamide; at 0 ℃; for 4.5h; Further stages.;
DOI:10.1016/j.tetlet.2007.05.166

Reference yield:

: 83476-52-2
propargyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

: 948297-89-0
3-(benzyloxy)propyl 2,3,4,6-tetrakis-O-[tert-butyl(dimethyl)silyl]-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 84 percent / hydrogen; quinoline / Pd/CaCO₃ / methanol / 2 h / 20 °C / 760.05 Torr

2.1: KOH / methanol / 20 °C

3.1: 341 mg / TEA / tetrahydrofuran / 2.5 h / 0 °C

4.1: BH₃*THF / tetrahydrofuran / 4 h / 0 °C

4.2: 60 percent / aq. NaOH; aq. hydrogen peroxide / 0.5 h

5.1: NaH / dimethylformamide / 0 °C

5.2: 79 percent / dimethylformamide / 4.5 h / 0 °C

With quinoline; potassium hydroxide; borane-THF; TEA; hydrogen; sodium hydride; Lindlar's catalyst; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2007.05.166

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 948297-89-0
3-(benzyloxy)propyl 2,3,4,6-tetrakis-O-[tert-butyl(dimethyl)silyl]-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 341 mg / TEA / tetrahydrofuran / 2.5 h / 0 °C

2.1: BH₃*THF / tetrahydrofuran / 4 h / 0 °C

2.2: 60 percent / aq. NaOH; aq. hydrogen peroxide / 0.5 h

3.1: NaH / dimethylformamide / 0 °C

3.2: 79 percent / dimethylformamide / 4.5 h / 0 °C

With borane-THF; TEA; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2007.05.166