tert-butyl 3-(carbobenzyloxyamino)-4-C-carbomethoxy-2,3,4,6-tetradeoxy-6-iodo-2-C-methyl-α-D-glucopyranoside

Base Information

Chemical Name:tert-butyl 3-(carbobenzyloxyamino)-4-C-carbomethoxy-2,3,4,6-tetradeoxy-6-iodo-2-C-methyl-α-D-glucopyranoside
CAS No.:119794-80-8
Molecular Formula:C₂₁H₃₀INO₆
Molecular Weight:519.377
Hs Code.:

Synonyms:tert-butyl 3-(carbobenzyloxyamino)-4-C-carbomethoxy-2,3,4,6-tetradeoxy-6-iodo-2-C-methyl-α-D-glucopyranoside

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

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

There total 17 articles about tert-butyl 3-(carbobenzyloxyamino)-4-C-carbomethoxy-2,3,4,6-tetradeoxy-6-iodo-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: 88.0%

: 119794-79-5
(2S,3S,4R,5R,6R)-4-Benzyloxycarbonylamino-6-tert-butoxy-2-hydroxymethyl-5-methyl-tetrahydro-pyran-3-carboxylic acid methyl ester

: 119794-80-8
tert-butyl 3-(carbobenzyloxyamino)-4-C-carbomethoxy-2,3,4,6-tetradeoxy-6-iodo-2-C-methyl-α-D-glucopyranoside

Guidance literature:: With 1H-imidazole; iodine; triphenylphosphine; In tetrahydrofuran; benzene; for 1h; Ambient temperature;
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

: 119794-80-8
tert-butyl 3-(carbobenzyloxyamino)-4-C-carbomethoxy-2,3,4,6-tetradeoxy-6-iodo-2-C-methyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 14 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: 70 percent / DIBAL / CH₂Cl₂; hexane / 0.17 h / -78 °C

11: NaIO₄, RuCl₃*3H₂O / acetonitrile; CCl₄; H₂O / 0.25 h

12: diethyl ether / 0.17 h

13: 81 percent / n-Bu₄NF / tetrahydrofuran / 1 h / 0 °C

14: 88 percent / imidazole, triphenylphosphine, iodine / tetrahydrofuran; benzene / 1 h / Ambient temperature

With pyridine; 1H-imidazole; ruthenium trichloride; sodium periodate; thionyl chloride; benzophenone; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; iodine; diisobutylaluminium hydride; ethylene glycol; acetic acid; triethylamine; triphenylphosphine; nickel; In tetrahydrofuran; pyridine; methanol; tetrachloromethane; diethyl ether; hexane; dichloromethane; water; acetonitrile; benzene;
DOI:10.1021/jo00270a019

Reference yield:

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

: 119794-80-8
tert-butyl 3-(carbobenzyloxyamino)-4-C-carbomethoxy-2,3,4,6-tetradeoxy-6-iodo-2-C-methyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 13 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: 70 percent / DIBAL / CH₂Cl₂; hexane / 0.17 h / -78 °C

10: NaIO₄, RuCl₃*3H₂O / acetonitrile; CCl₄; H₂O / 0.25 h

11: diethyl ether / 0.17 h

12: 81 percent / n-Bu₄NF / tetrahydrofuran / 1 h / 0 °C

13: 88 percent / imidazole, triphenylphosphine, iodine / tetrahydrofuran; benzene / 1 h / Ambient temperature

With pyridine; 1H-imidazole; ruthenium trichloride; sodium periodate; thionyl chloride; benzophenone; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; iodine; diisobutylaluminium hydride; acetic acid; triethylamine; triphenylphosphine; nickel; In tetrahydrofuran; pyridine; methanol; tetrachloromethane; diethyl ether; hexane; dichloromethane; water; acetonitrile; benzene;
DOI:10.1021/jo00270a019