methyl 6-azido-3,6-dideoxy-3-(3,4,6-tri-O-benzyl-5a-carba-α-D-mannopyranosylamino)-α-D-mannopyranoside

Base Information

• Chemical Name: methyl 6-azido-3,6-dideoxy-3-(3,4,6-tri-O-benzyl-5a-carba-α-D-mannopyranosylamino)-α-D-mannopyranoside
• CAS No.: 172291-50-8
• Molecular Formula: C₃₅H₄₄N₄O₈
• Molecular Weight: 648.756
• Mol file: 172291-50-8.mol

Synonyms:methyl 6-azido-3,6-dideoxy-3-(3,4,6-tri-O-benzyl-5a-carba-α-D-mannopyranosylamino)-α-D-mannopyranoside

Chemical Property of methyl 6-azido-3,6-dideoxy-3-(3,4,6-tri-O-benzyl-5a-carba-α-D-mannopyranosylamino)-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 6-azido-3,6-dideoxy-3-(3,4,6-tri-O-benzyl-5a-carba-α-D-mannopyranosylamino)-α-D-mannopyranoside

There total 7 articles about methyl 6-azido-3,6-dideoxy-3-(3,4,6-tri-O-benzyl-5a-carba-α-D-mannopyranosylamino)-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: 61.0%

(1R,2R,3S,4R,5R)-1,2-anhydro-3,4-di-O-benzyl-5-benzyloxymethylcyclohexan-1,2,3,4-tetraol (152203-03-7) + methyl 3-amino-6-azido-3,6-dideoxy-α-D-mannopyranoside (172291-44-0) → methyl 6-azido-3,6-dideoxy-3-(3,4,6-tri-O-benzyl-5a-carba-α-D-mannopyranosylamino)-α-D-mannopyranoside (172291-50-8)

Guidance literature:

In isopropyl alcohol; at 120 ℃; for 48h;

DOI:10.1016/0008-6215(95)00121-9

Reference yield:

methyl 3-amino-3-deoxy-α-D-mannopyranoside (14193-51-2,686298-97-5) → methyl 6-azido-3,6-dideoxy-3-(3,4,6-tri-O-benzyl-5a-carba-α-D-mannopyranosylamino)-α-D-mannopyranoside (172291-50-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / ethanol / 1 h / Ambient temperature

2: 87 percent / pyridine / 7 h / 0 °C

3: 93 percent / NaN₃ / H₂O; dimethylformamide / 4 h / 100 °C

4: 90 percent / TFA / CHCl₃ / 0.75 h / Ambient temperature

5: 61 percent / propan-2-ol / 48 h / 120 °C

With pyridine; sodium azide; trifluoroacetic acid; In ethanol; chloroform; water; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1016/0008-6215(95)00121-9

Reference yield:

benzyl bromide (100-39-0) → methyl 6-azido-3,6-dideoxy-3-(3,4,6-tri-O-benzyl-5a-carba-α-D-mannopyranosylamino)-α-D-mannopyranoside (172291-50-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 1 h

2: 61 percent / propan-2-ol / 48 h / 120 °C

With sodium hydride; In isopropyl alcohol;

DOI:10.1016/0008-6215(95)00121-9

upstream raw materials:

(1R,2R,3S,4R,5R)-1,2-anhydro-3,4-di-O-benzyl-5-benzyloxymethylcyclohexan-1,2,3,4-tetraol

methyl 3-amino-6-azido-3,6-dideoxy-α-D-mannopyranoside

methyl 3-amino-3-deoxy-α-D-mannopyranoside

benzyl bromide

Downstream raw materials:

methyl 3,6-dideoxy-3,6-bis(3,4,6-tri-O-benzyl-5a-carba-α-D-mannopyranosylamino)-α-D-mannopyranoside

(2R,3S,4S,5S,6S)-2-Aminomethyl-4-((1S,2R,3R,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-2-hydroxy-cyclohexylamino)-6-methoxy-tetrahydro-pyran-3,5-diol