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

Base Information

• Chemical Name: methyl 3,6-dideoxy-3,6-bis(3,4,6-tri-O-benzyl-5a-carba-α-D-mannopyranosylamino)-α-D-mannopyranoside
• CAS No.: 172342-17-5
• Molecular Formula: C₆₃H₇₆N₂O₁₂
• Molecular Weight: 1053.3
• Mol file: 172342-17-5.mol

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

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

There total 11 articles about methyl 3,6-dideoxy-3,6-bis(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: 72.0%

methyl 3,6-diamino-3,6-dideoxy-α-D-mannopyranoside (14133-34-7) + (1R,2R,3S,4R,5R)-1,2-anhydro-3,4-di-O-benzyl-5-benzyloxymethylcyclohexan-1,2,3,4-tetraol (152203-03-7) → methyl 3,6-dideoxy-3,6-bis(3,4,6-tri-O-benzyl-5a-carba-α-D-mannopyranosylamino)-α-D-mannopyranoside (172342-17-5)

Guidance literature:

In isopropyl alcohol; at 120 ℃; for 216h;

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

Reference yield: 70.0%

(1R,2R,3S,4R,5R)-1,2-anhydro-3,4-di-O-benzyl-5-benzyloxymethylcyclohexan-1,2,3,4-tetraol (152203-03-7) + (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 (172291-51-9) → methyl 3,6-dideoxy-3,6-bis(3,4,6-tri-O-benzyl-5a-carba-α-D-mannopyranosylamino)-α-D-mannopyranoside (172342-17-5)

Guidance literature:

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

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 3,6-dideoxy-3,6-bis(3,4,6-tri-O-benzyl-5a-carba-α-D-mannopyranosylamino)-α-D-mannopyranoside (172342-17-5)

Guidance literature:

Multi-step reaction with 7 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

6: H₂ / Raney-Ni T-4 / ethanol / 4 h / 760 Torr / Ambient temperature

7: 70 percent / propan-2-ol / 120 h / 120 °C

With pyridine; sodium azide; hydrogen; trifluoroacetic acid; Raney-Ni T-4; In ethanol; chloroform; water; N,N-dimethyl-formamide; isopropyl alcohol;

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

upstream raw materials:

methyl 3,6-diamino-3,6-dideoxy-α-D-mannopyranoside

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

(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

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