tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(carbobenzyloxyamino)-2,3,4-trideoxy-4-C-(hydroxymethyl)-2-C-methyl-α-D-glucopyranoside

Base Information

Chemical Name:tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(carbobenzyloxyamino)-2,3,4-trideoxy-4-C-(hydroxymethyl)-2-C-methyl-α-D-glucopyranoside
CAS No.:119794-74-0
Molecular Formula:C₂₆H₄₅NO₆Si
Molecular Weight:495.732
Hs Code.:

Synonyms:tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(carbobenzyloxyamino)-2,3,4-trideoxy-4-C-(hydroxymethyl)-2-C-methyl-α-D-glucopyranoside

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Chemical Property of tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(carbobenzyloxyamino)-2,3,4-trideoxy-4-C-(hydroxymethyl)-2-C-methyl-α-D-glucopyranoside

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Technology Process of tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(carbobenzyloxyamino)-2,3,4-trideoxy-4-C-(hydroxymethyl)-2-C-methyl-α-D-glucopyranoside

There total 20 articles about tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(carbobenzyloxyamino)-2,3,4-trideoxy-4-C-(hydroxymethyl)-2-C-methyl-α-D-glucopyranoside 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: 84.0%

: 114059-52-8
2,2-Dimethyl-propionic acid (2S,3R,4S,5R,6R)-4-benzyloxycarbonylamino-6-tert-butoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-tetrahydro-pyran-3-ylmethyl ester

: 119794-74-0
tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(carbobenzyloxyamino)-2,3,4-trideoxy-4-C-(hydroxymethyl)-2-C-methyl-α-D-glucopyranoside

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 ℃;
DOI:10.1021/jo00244a061

Reference yield: 70.0%

: 114059-51-7,114059-52-8
2,2-Dimethyl-propionic acid (2S,3R,4S,6R)-4-benzyloxycarbonylamino-6-tert-butoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-tetrahydro-pyran-3-ylmethyl ester

: 119794-75-1
tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(carbobenzyloxyamino)-2,3,4-trideoxy-4-C-(hydroxymethyl)-2-C-methyl-α-D-mannopyranoside

: 119794-74-0
tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(carbobenzyloxyamino)-2,3,4-trideoxy-4-C-(hydroxymethyl)-2-C-methyl-α-D-glucopyranoside

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 0.166667h;
DOI:10.1021/jo00270a019

Reference yield:

: 119794-57-9
tert-butyl 6-O-(tert-butyldimethylsilyl)-3,4-dideoxy-α-D-glycero-hex-3-enopyranosid-2-ulose

: 119794-74-0
tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(carbobenzyloxyamino)-2,3,4-trideoxy-4-C-(hydroxymethyl)-2-C-methyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: Irradiation

2: pyridine / CH₂Cl₂

3: 94 percent / t-BuOH / tetrahydrofuran / 1.) from -78 deg C to 0 deg C, 2.) -78 deg C

4: 94 percent / diethyl ether

5: 86 percent / SOCl₂, pyridine

6: H₂ / Raney Ni / methanol

7: methanol

8: 84 percent / DIBAL / CH₂Cl₂ / -78 °C

With pyridine; thionyl chloride; hydrogen; diisobutylaluminium hydride; tert-butyl alcohol; nickel; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1021/jo00244a061