2,4,6-tri-O-benzyl-3-O-methoxycarbonylmethyl-β-D-galactopyranosyl-(1-1)-6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranoside

Base Information

Chemical Name:2,4,6-tri-O-benzyl-3-O-methoxycarbonylmethyl-β-D-galactopyranosyl-(1-1)-6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranoside
CAS No.:220129-85-1
Molecular Formula:C₅₇H₆₁N₃O₁₂
Molecular Weight:980.124
Hs Code.:

Synonyms:2,4,6-tri-O-benzyl-3-O-methoxycarbonylmethyl-β-D-galactopyranosyl-(1-1)-6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranoside

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Chemical Property of 2,4,6-tri-O-benzyl-3-O-methoxycarbonylmethyl-β-D-galactopyranosyl-(1-1)-6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranoside

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Technology Process of 2,4,6-tri-O-benzyl-3-O-methoxycarbonylmethyl-β-D-galactopyranosyl-(1-1)-6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranoside

There total 10 articles about 2,4,6-tri-O-benzyl-3-O-methoxycarbonylmethyl-β-D-galactopyranosyl-(1-1)-6-azido-2,3,4-tri-O-benzyl-6-deoxy-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: 4.1%

: 220129-80-6
6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranosyl fluoride

: ((2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-trimethylsilanyloxy-tetrahydro-pyran-4-yloxy)-acetic acid methyl ester

: 220129-85-1
2,4,6-tri-O-benzyl-3-O-methoxycarbonylmethyl-β-D-galactopyranosyl-(1-1)-6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranoside

: 2,4,6-tri-O-benzyl-3-O-methoxycarbonylmethyl-α-D-galactopyranosyl-(1-1)-6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranoside

Guidance literature:: With bis(cyclopentadienyl)hafnium dichloride; silver perchlorate; In dichloromethane; 1.) -78 deg C, 2 h, 2.) -70 to -50 deg C, 1 h;
DOI:10.1016/S0040-4020(98)00990-9

Reference yield:

: 34212-64-1,641635-63-4
methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside

: 220129-85-1
2,4,6-tri-O-benzyl-3-O-methoxycarbonylmethyl-β-D-galactopyranosyl-(1-1)-6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 1.47 g / Et₃N / CH₂Cl₂ / 3 h / Ambient temperature

2: 93 percent / NaN₃ / dimethylformamide / 4 h / 90 °C

3: H₂SO₄ / acetic anhydride / 4 h / Ambient temperature

4: MeONa / methanol / 0.08 h / Ambient temperature

5: 88 percent / diethylaminosulfurtrifluoride / CH₂Cl₂ / 0.17 h

6: 55 percent / Cp₂HfCl₂, AgClO₄ / CH₂Cl₂ / 1.) -78 deg C, 2 h, 2.) -70 to -50 deg C, 1 h

With sodium azide; bis(cyclopentadienyl)hafnium dichloride; diethylamino-sulfur trifluoride; sulfuric acid; sodium methylate; silver perchlorate; triethylamine; In methanol; dichloromethane; acetic anhydride; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(98)00990-9

Reference yield:

: 65518-53-8
methyl 2,3,4-tri-O-benzyl-6-O-tosyl-α-D-mannopyranoside

: 220129-85-1
2,4,6-tri-O-benzyl-3-O-methoxycarbonylmethyl-β-D-galactopyranosyl-(1-1)-6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / NaN₃ / dimethylformamide / 4 h / 90 °C

2: H₂SO₄ / acetic anhydride / 4 h / Ambient temperature

3: MeONa / methanol / 0.08 h / Ambient temperature

4: 88 percent / diethylaminosulfurtrifluoride / CH₂Cl₂ / 0.17 h

5: 55 percent / Cp₂HfCl₂, AgClO₄ / CH₂Cl₂ / 1.) -78 deg C, 2 h, 2.) -70 to -50 deg C, 1 h

With sodium azide; bis(cyclopentadienyl)hafnium dichloride; diethylamino-sulfur trifluoride; sulfuric acid; sodium methylate; silver perchlorate; In methanol; dichloromethane; acetic anhydride; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(98)00990-9