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

Base Information

Chemical Name:tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(carbobenzyloxyamino)-4-C-carbomethoxy-2,3,4-trideoxy-2-C-methyl-α-D-glucopyranoside
CAS No.:114059-53-9
Molecular Formula:C₂₇H₄₅NO₇Si
Molecular Weight:523.742
Hs Code.:

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

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

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

There total 22 articles about tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(carbobenzyloxyamino)-4-C-carbomethoxy-2,3,4-trideoxy-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:

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

: 114059-53-9
tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(carbobenzyloxyamino)-4-C-carbomethoxy-2,3,4-trideoxy-2-C-methyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 9 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

9: 1.) RuCl₂*H₂O, NaIO₄ / 1.) CCl₄, MeCN, H₂O, 2.) Et₂O

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

Reference yield:

: 114094-16-5
tert-butyl 6-O-(tert-butyldimethylsilyl)-3,4-dideoxy-4-C-<(trimethylacetoxy)methyl>-α-D-erythro-hexopyranosid-2-ulose

: 114059-53-9
tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(carbobenzyloxyamino)-4-C-carbomethoxy-2,3,4-trideoxy-2-C-methyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

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

2: 94 percent / diethyl ether

3: 86 percent / SOCl₂, pyridine

4: H₂ / Raney Ni / methanol

5: methanol

6: 84 percent / DIBAL / CH₂Cl₂ / -78 °C

7: 1.) RuCl₂*H₂O, NaIO₄ / 1.) CCl₄, MeCN, H₂O, 2.) Et₂O

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

Reference yield:

: 114094-38-1
tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(N,N'-dicarbobenzyloxyhydrazino)-2,3,4-trideoxy-4-C-<(trimethylacetoxy)methyl>-2-C-methylene-α-D-arabino-hexopyranoside

: 114059-53-9
tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(carbobenzyloxyamino)-4-C-carbomethoxy-2,3,4-trideoxy-2-C-methyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: H₂ / Raney Ni / methanol

2: methanol

3: 84 percent / DIBAL / CH₂Cl₂ / -78 °C

4: 1.) RuCl₂*H₂O, NaIO₄ / 1.) CCl₄, MeCN, H₂O, 2.) Et₂O

With ruthenium(II) chloride; sodium periodate; hydrogen; diisobutylaluminium hydride; nickel; In methanol; dichloromethane;
DOI:10.1021/jo00244a061