tert-butyl ((2R,4R,5S,6R)-5-(benzyloxy)-6-methyl-2-(5-(dimethyl(vinyl)silyl)furan-2-yl)tetrahydro-2H-pyran-4-yl)(methyl)carbamate

Base Information

Chemical Name:tert-butyl ((2R,4R,5S,6R)-5-(benzyloxy)-6-methyl-2-(5-(dimethyl(vinyl)silyl)furan-2-yl)tetrahydro-2H-pyran-4-yl)(methyl)carbamate
CAS No.:1255790-39-6
Molecular Formula:C₂₇H₃₉NO₅Si
Molecular Weight:485.696
Hs Code.:

Synonyms:tert-butyl ((2R,4R,5S,6R)-5-(benzyloxy)-6-methyl-2-(5-(dimethyl(vinyl)silyl)furan-2-yl)tetrahydro-2H-pyran-4-yl)(methyl)carbamate

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Chemical Property of tert-butyl ((2R,4R,5S,6R)-5-(benzyloxy)-6-methyl-2-(5-(dimethyl(vinyl)silyl)furan-2-yl)tetrahydro-2H-pyran-4-yl)(methyl)carbamate

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Technology Process of tert-butyl ((2R,4R,5S,6R)-5-(benzyloxy)-6-methyl-2-(5-(dimethyl(vinyl)silyl)furan-2-yl)tetrahydro-2H-pyran-4-yl)(methyl)carbamate

There total 12 articles about tert-butyl ((2R,4R,5S,6R)-5-(benzyloxy)-6-methyl-2-(5-(dimethyl(vinyl)silyl)furan-2-yl)tetrahydro-2H-pyran-4-yl)(methyl)carbamate 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: 82.0%

: 1719-58-0
Chlorodimethylvinylsilane

: 1255790-40-9
tert-butyl (2R,4R,5S,6R)-5-benzyloxy-2-(furan-2-yl)-6-methyltetrahydro-2H-pyran-4-yl(methyl)carbamate

: 1255790-39-6
tert-butyl ((2R,4R,5S,6R)-5-(benzyloxy)-6-methyl-2-(5-(dimethyl(vinyl)silyl)furan-2-yl)tetrahydro-2H-pyran-4-yl)(methyl)carbamate

Guidance literature:: tert-butyl (2R,4R,5S,6R)-5-benzyloxy-2-(furan-2-yl)-6-methyltetrahydro-2H-pyran-4-yl(methyl)carbamate; With sec.-butyllithium; In tetrahydrofuran; cyclohexane; at -78 - -50 ℃; for 2.5h; Inert atmosphere;

Chlorodimethylvinylsilane; In tetrahydrofuran; cyclohexane; at -78 - 20 ℃; Inert atmosphere;
DOI:10.1021/ja107926f

Reference yield:

: 1330578-73-8
(2R,4R,5S,6R)-4-azido-5-benzyloxy-2-(furan-2-yl)-6-methyltetrahydro-2H-pyran

: 1255790-39-6
tert-butyl ((2R,4R,5S,6R)-5-(benzyloxy)-6-methyl-2-(5-(dimethyl(vinyl)silyl)furan-2-yl)tetrahydro-2H-pyran-4-yl)(methyl)carbamate

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium aluminium tetrahydride / diethyl ether / 0 - 20 °C / Inert atmosphere

1.2: 0 °C

2.1: dichloromethane / 18 h / 20 °C / Inert atmosphere

3.1: sodium hydride / dfm / 1 h / 20 °C / Inert atmosphere

4.1: sec.-butyllithium / tetrahydrofuran; cyclohexane / 2.5 h / -78 - -50 °C / Inert atmosphere

4.2: -78 - 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; sec.-butyllithium; sodium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; cyclohexane; dfm;
DOI:10.1016/j.tet.2011.05.117

Reference yield:

: C₁₇H₂₁NO₃

: 1255790-39-6
tert-butyl ((2R,4R,5S,6R)-5-(benzyloxy)-6-methyl-2-(5-(dimethyl(vinyl)silyl)furan-2-yl)tetrahydro-2H-pyran-4-yl)(methyl)carbamate

Guidance literature:: Multi-step reaction with 3 steps

1.1: dichloromethane / 18 h / 20 °C / Inert atmosphere

2.1: sodium hydride / dfm / 1 h / 20 °C / Inert atmosphere

3.1: sec.-butyllithium / tetrahydrofuran; cyclohexane / 2.5 h / -78 - -50 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

With sec.-butyllithium; sodium hydride; In tetrahydrofuran; dichloromethane; cyclohexane; dfm;
DOI:10.1016/j.tet.2011.05.117