tert-butyldimethylsilyl 2,3,4,6-tetra-O-benzyl-5a-carba-α-D-mannopyranoside

Base Information

Chemical Name:tert-butyldimethylsilyl 2,3,4,6-tetra-O-benzyl-5a-carba-α-D-mannopyranoside
CAS No.:1313195-35-5
Molecular Formula:C₄₁H₅₂O₅Si
Molecular Weight:652.946
Hs Code.:

Synonyms:tert-butyldimethylsilyl 2,3,4,6-tetra-O-benzyl-5a-carba-α-D-mannopyranoside

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Chemical Property of tert-butyldimethylsilyl 2,3,4,6-tetra-O-benzyl-5a-carba-α-D-mannopyranoside

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Technology Process of tert-butyldimethylsilyl 2,3,4,6-tetra-O-benzyl-5a-carba-α-D-mannopyranoside

There total 8 articles about tert-butyldimethylsilyl 2,3,4,6-tetra-O-benzyl-5a-carba-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: 73.0%

: 1313195-34-4
tert-butyldimethylsilyl 4,6-di-O-benzyl-5a-carba-α-D-mannopyranoside

: 100-39-0
benzyl bromide

: 1313195-35-5
tert-butyldimethylsilyl 2,3,4,6-tetra-O-benzyl-5a-carba-α-D-mannopyranoside

Guidance literature:: tert-butyldimethylsilyl 4,6-di-O-benzyl-5a-carba-α-D-mannopyranoside; With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 0 ℃; for 2h; Inert atmosphere;

benzyl bromide; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1016/j.carres.2011.04.011

Reference yield:

: 1313195-33-3
(1S,4S,5R)-4-O-benzyl-5-benzyloxymethyl-1-O-(tert-butyldimethylsilyl)cyclohex-2-en-1,4-diol

: 1313195-35-5
tert-butyldimethylsilyl 2,3,4,6-tetra-O-benzyl-5a-carba-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium osmate(VI); 4-methylmorpholine N-oxide / water; acetone / 16 h / 20 °C

2.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

With potassium osmate(VI); tetra-(n-butyl)ammonium iodide; sodium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; acetone;
DOI:10.1016/j.carres.2011.04.011

Reference yield:

: 338460-84-7
(4S,6R)-4-tert-butyldimethylsilyloxy-6-hydroxymethyl-2-cyclohexenone

: 1313195-35-5
tert-butyldimethylsilyl 2,3,4,6-tetra-O-benzyl-5a-carba-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium tris(acetoxy)borohydride / acetic acid / 0.5 h

2.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

3.1: potassium osmate(VI); 4-methylmorpholine N-oxide / water; acetone / 16 h / 20 °C

4.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

4.2: 0 - 20 °C / Inert atmosphere

With potassium osmate(VI); tetra-(n-butyl)ammonium iodide; sodium tris(acetoxy)borohydride; sodium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; acetic acid; acetone;
DOI:10.1016/j.carres.2011.04.011