tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(N,N'-dicarbobenzyloxyhydrazino)-2,3,4-trideoxy-4-C-<(trimethylacetoxy)methyl>-2-C-<(trimethylsilyl)methylene>-α-D-arabino-hexopyranoside

Base Information

Chemical Name:tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(N,N'-dicarbobenzyloxyhydrazino)-2,3,4-trideoxy-4-C-<(trimethylacetoxy)methyl>-2-C-<(trimethylsilyl)methylene>-α-D-arabino-hexopyranoside
CAS No.:119794-68-2
Molecular Formula:C₄₂H₆₆N₂O₉Si₂
Molecular Weight:799.165
Hs Code.:

tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(N,N'-dicarbobenzyloxyhydrazino)-2,3,4-trideoxy-4-C-<(trimethylacetoxy)methyl>-2-C-<(trimethylsilyl)methylene>-α-D-arabino-hexopyranoside

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Chemical Property of tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(N,N'-dicarbobenzyloxyhydrazino)-2,3,4-trideoxy-4-C-<(trimethylacetoxy)methyl>-2-C-<(trimethylsilyl)methylene>-α-D-arabino-hexopyranoside

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Technology Process of tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(N,N'-dicarbobenzyloxyhydrazino)-2,3,4-trideoxy-4-C-<(trimethylacetoxy)methyl>-2-C-<(trimethylsilyl)methylene>-α-D-arabino-hexopyranoside

There total 11 articles about tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(N,N'-dicarbobenzyloxyhydrazino)-2,3,4-trideoxy-4-C-<(trimethylacetoxy)methyl>-2-C-<(trimethylsilyl)methylene>-α-D-arabino-hexopyranoside 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:

: 2449-05-0
dibenzyl azodicarboxylate

: 119794-68-2
tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(N,N'-dicarbobenzyloxyhydrazino)-2,3,4-trideoxy-4-C-<(trimethylacetoxy)methyl>-2-C-<(trimethylsilyl)methylene>-α-D-arabino-hexopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) t-BuOK / 1.) THF, -78 deg C to 0 deg C, 20 min, 2.) -78 deg C, 10 min

2: diethyl ether / 6 h / Ambient temperature

3: 69.5 mg / thionyl chloride / pyridine / 1.) 0 deg C, 15 min, 2.) without cooling, 10 min

With thionyl chloride; potassium tert-butylate; In pyridine; diethyl ether;
DOI:10.1021/jo00270a019

Reference yield:

: 79698-71-8
tert-butyl 2,4,6-tri-O-acetyl-3-deoxy-α-D-erythro-hex-2-enopyranoside

: 119794-68-2
tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(N,N'-dicarbobenzyloxyhydrazino)-2,3,4-trideoxy-4-C-<(trimethylacetoxy)methyl>-2-C-<(trimethylsilyl)methylene>-α-D-arabino-hexopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 40 percent / ethylene glycol, triethylamine, water / methanol / 0.67 h / Ambient temperature

2: 72 percent / pyridine / CH₂Cl₂ / 19 h / Ambient temperature

3: 0.602 g / benzophenone / 1 h / Irradiation

4: 80 percent / pyridine / CH₂Cl₂ / 12 h / Ambient temperature

5: 1.) t-BuOK / 1.) THF, -78 deg C to 0 deg C, 20 min, 2.) -78 deg C, 10 min

6: diethyl ether / 6 h / Ambient temperature

7: 69.5 mg / thionyl chloride / pyridine / 1.) 0 deg C, 15 min, 2.) without cooling, 10 min

With pyridine; thionyl chloride; benzophenone; potassium tert-butylate; water; ethylene glycol; triethylamine; In pyridine; methanol; diethyl ether; dichloromethane;
DOI:10.1021/jo00270a019

Reference yield:

: 3282-30-2
pivaloyl chloride

: 119794-68-2
tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(N,N'-dicarbobenzyloxyhydrazino)-2,3,4-trideoxy-4-C-<(trimethylacetoxy)methyl>-2-C-<(trimethylsilyl)methylene>-α-D-arabino-hexopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 80 percent / pyridine / CH₂Cl₂ / 12 h / Ambient temperature

2: 1.) t-BuOK / 1.) THF, -78 deg C to 0 deg C, 20 min, 2.) -78 deg C, 10 min

3: diethyl ether / 6 h / Ambient temperature

4: 69.5 mg / thionyl chloride / pyridine / 1.) 0 deg C, 15 min, 2.) without cooling, 10 min

With pyridine; thionyl chloride; potassium tert-butylate; In pyridine; diethyl ether; dichloromethane;
DOI:10.1021/jo00270a019