1-methylethyl 3,4,6-tri-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: 1-methylethyl 3,4,6-tri-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranoside
• CAS No.: 130259-41-5
• Molecular Formula: C₂₃H₃₁NO₁₀
• Molecular Weight: 481.5
• Mol file: 130259-41-5.mol

Synonyms:1-methylethyl 3,4,6-tri-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranoside

Chemical Property of 1-methylethyl 3,4,6-tri-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-methylethyl 3,4,6-tri-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranoside

There total 4 articles about 1-methylethyl 3,4,6-tri-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-β-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: 59.0%

2-(acetoxymethyl)-5-{[(benzyloxy)carbonyl]amino}tetrahydropyran-3,4,6-triyl triacetate (35946-66-8) + isopropyl alcohol (67-63-0,8013-70-5) → 1-methylethyl 3,4,6-tri-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranoside (130259-41-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -35 ℃;

DOI:10.1016/0008-6215(90)84077-8

Reference yield: 28.0%

3,4,6-tri-O-acetyl-2-(benzoyloxycarbonyl)amino-2-deoxy-α-D-glucopyranosyl bromide (73446-41-0) + isopropyl alcohol (67-63-0,8013-70-5) → 1-methylethyl 3,4,6-tri-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranoside (130259-41-5) + tetrahydro-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[2,1-d]-1,3-oxazol-2-one (76548-23-7,10163-09-4)

Guidance literature:

With mercury(II) cyanide; In dichloromethane; Ambient temperature;

DOI:10.1016/0008-6215(90)84077-8

Reference yield:

(2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-((E)-(4-methoxybenzylidene)amino)tetrahydro-2Hpyran-2,4,5-triyl triacetate (7597-81-1,34948-61-3,55628-19-8,74554-00-0,103382-86-1,114297-26-6) → 1-methylethyl 3,4,6-tri-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranoside (130259-41-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 5.5 M HCl / acetone / Heating

2: 1. NaHCO₃ / 1. H₂O 2. CHCl₃, 1 h, room temperature

3: 59 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / -35 °C

With hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; sodium hydrogencarbonate; In dichloromethane; acetone;

DOI:10.1016/0008-6215(90)84077-8

upstream raw materials:

2-(acetoxymethyl)-5-{[(benzyloxy)carbonyl]amino}tetrahydropyran-3,4,6-triyl triacetate

isopropyl alcohol

3,4,6-tri-O-acetyl-2-(benzoyloxycarbonyl)amino-2-deoxy-α-D-glucopyranosyl bromide

(2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-((E)-(4-methoxybenzylidene)amino)tetrahydro-2Hpyran-2,4,5-triyl triacetate