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

Base Information

Chemical Name:tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(carbobenzyloxyamino)-2,3,4-trideoxy-4-C-(hydroxymethyl)-2-C-methyl-α-D-mannopyranoside
CAS No.:119794-75-1
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-mannopyranoside

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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-mannopyranoside

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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-mannopyranoside

There total 13 articles about tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(carbobenzyloxyamino)-2,3,4-trideoxy-4-C-(hydroxymethyl)-2-C-methyl-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: 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:

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

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

Guidance literature:: Multi-step reaction with 10 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: 190.2 mg / thionyl chloride / pyridine / 1.) 0 deg C, 15 min, 2.) without cooling, 10 min

8: hydrogen, acetic acid / Raney nickel / methanol / 8 h

9: triethylamine / methanol / 1.5 h / 0 °C

10: 14 percent / DIBAL / CH₂Cl₂; hexane / 0.17 h / -78 °C

With pyridine; thionyl chloride; benzophenone; potassium tert-butylate; water; hydrogen; diisobutylaluminium hydride; ethylene glycol; acetic acid; triethylamine; nickel; In pyridine; methanol; diethyl ether; hexane; dichloromethane;
DOI:10.1021/jo00270a019

Reference yield:

: 119794-56-8
tert-butyl 3,4-dideoxy-α-D-glycero-hex-3-enopyranosid-2-ulose

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

Guidance literature:: Multi-step reaction with 9 steps

1: 72 percent / pyridine / CH₂Cl₂ / 19 h / Ambient temperature

2: 0.602 g / benzophenone / 1 h / Irradiation

3: 80 percent / pyridine / CH₂Cl₂ / 12 h / Ambient temperature

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

5: diethyl ether / 6 h / Ambient temperature

6: 190.2 mg / thionyl chloride / pyridine / 1.) 0 deg C, 15 min, 2.) without cooling, 10 min

7: hydrogen, acetic acid / Raney nickel / methanol / 8 h

8: triethylamine / methanol / 1.5 h / 0 °C

9: 14 percent / DIBAL / CH₂Cl₂; hexane / 0.17 h / -78 °C

With pyridine; thionyl chloride; benzophenone; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; acetic acid; triethylamine; nickel; In pyridine; methanol; diethyl ether; hexane; dichloromethane;
DOI:10.1021/jo00270a019