2-O-(benzyloxycarbonyl)-1,7-O-isopropylidene-1L-(1,3,4/2)-4-amino-6-C-(hydroxymethyl)-5-cyclohexene-1,2,3-triol 3,4-carbamate

Base Information

• Chemical Name: 2-O-(benzyloxycarbonyl)-1,7-O-isopropylidene-1L-(1,3,4/2)-4-amino-6-C-(hydroxymethyl)-5-cyclohexene-1,2,3-triol 3,4-carbamate
• CAS No.: 89859-53-0
• Molecular Formula: C₁₉H₂₁NO₇
• Molecular Weight: 375.378
• Mol file: 89859-53-0.mol

Synonyms:

Chemical Property of 2-O-(benzyloxycarbonyl)-1,7-O-isopropylidene-1L-(1,3,4/2)-4-amino-6-C-(hydroxymethyl)-5-cyclohexene-1,2,3-triol 3,4-carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-(benzyloxycarbonyl)-1,7-O-isopropylidene-1L-(1,3,4/2)-4-amino-6-C-(hydroxymethyl)-5-cyclohexene-1,2,3-triol 3,4-carbamate

There total 4 articles about 2-O-(benzyloxycarbonyl)-1,7-O-isopropylidene-1L-(1,3,4/2)-4-amino-6-C-(hydroxymethyl)-5-cyclohexene-1,2,3-triol 3,4-carbamate 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:

benzyl chloroformate (501-53-1,94274-21-2) + 1,7-O-isopropylidene-1L-(1,3,4/2)-4-amino-6-C-(hydroxymethyl)-5-cyclohexene-1,2,3-triol 3,4-carbamate (89859-55-2) → 2-O-(benzyloxycarbonyl)-1,7-O-isopropylidene-1L-(1,3,4/2)-4-amino-6-C-(hydroxymethyl)-5-cyclohexene-1,2,3-triol 3,4-carbamate (89859-53-0)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at -20 - -10 ℃; for 2h;

DOI:10.1016/0008-6215(85)85122-3

Reference yield:

valienamine (38231-86-6) → 2-O-(benzyloxycarbonyl)-1,7-O-isopropylidene-1L-(1,3,4/2)-4-amino-6-C-(hydroxymethyl)-5-cyclohexene-1,2,3-triol 3,4-carbamate (89859-53-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 146 g / sodium hydrogencarbonate / toluene; H₂O / 1.) 5-10 deg C, 1 h, 2.) room temp., 3 h

2: 12 g / M sodium hydroxide / 2 h / Ambient temperature

3: 11.3 g / p-toluenesulfonic acid / dimethylformamide / 2 h / 100 °C

4: 4.3 g / triethylamine / dimethylformamide / 2 h / -20 - -10 °C

With sodium hydroxide; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; In water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0008-6215(85)85122-3

Reference yield:

1L-(1,3,4/2)-4-amino-6-C-(hydroxymethyl)-5-cyclohexene-1,2,3-triol 3,4-carbamate (89859-54-1) → 2-O-(benzyloxycarbonyl)-1,7-O-isopropylidene-1L-(1,3,4/2)-4-amino-6-C-(hydroxymethyl)-5-cyclohexene-1,2,3-triol 3,4-carbamate (89859-53-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 11.3 g / p-toluenesulfonic acid / dimethylformamide / 2 h / 100 °C

2: 4.3 g / triethylamine / dimethylformamide / 2 h / -20 - -10 °C

With toluene-4-sulfonic acid; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(85)85122-3

upstream raw materials:

benzyl chloroformate

1,7-O-isopropylidene-1L-(1,3,4/2)-4-amino-6-C-(hydroxymethyl)-5-cyclohexene-1,2,3-triol 3,4-carbamate

valienamine

1L-(1,3,4/2)-4-amino-6-C-(hydroxymethyl)-5-cyclohexene-1,2,3-triol 3,4-carbamate

Downstream raw materials:

epivaliolamine