2-(benzyloxycarbonyl)aminoethyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-dibenzylphosphate-α-D-mannopyranoside

Base Information

Chemical Name:2-(benzyloxycarbonyl)aminoethyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-dibenzylphosphate-α-D-mannopyranoside
CAS No.:497096-21-6
Molecular Formula:C₄₆H₅₁N₂O₁₁P
Molecular Weight:838.892
Hs Code.:

Synonyms:2-(benzyloxycarbonyl)aminoethyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-dibenzylphosphate-α-D-mannopyranoside

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Chemical Property of 2-(benzyloxycarbonyl)aminoethyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-dibenzylphosphate-α-D-mannopyranoside

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Technology Process of 2-(benzyloxycarbonyl)aminoethyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-dibenzylphosphate-α-D-mannopyranoside

There total 9 articles about 2-(benzyloxycarbonyl)aminoethyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-dibenzylphosphate-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:

: {2-[(2S,3S,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-(bis-benzyloxy-phosphanyloxymethyl)-tetrahydro-pyran-2-yloxy]-ethyl}-carbamic acid benzyl ester

: 497096-21-6
2-(benzyloxycarbonyl)aminoethyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-dibenzylphosphate-α-D-mannopyranoside

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In acetonitrile; at -40 - 23 ℃; for 1.08333h;
DOI:10.1002/1521-3765(20021004)8:19<4424::AID-CHEM4424>3.0.CO;2-1

Reference yield:

: 77987-49-6
benzyl 2-hydroxyethylcarbamate

: 497096-21-6
2-(benzyloxycarbonyl)aminoethyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-dibenzylphosphate-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 54 percent / TMSOTf / CH₂Cl₂ / 0.5 h / 0 °C

2: NaBH₄; NiCl₂*6H₂O / methanol / 1 h / 0 - 10 °C

3: 8.15 g / methanol / 0.5 h / 5 °C

4: 93 percent / NaOMe / methanol / 0.5 h / 23 °C

5: tetrazole / acetonitrile / 0.5 h / 23 °C

6: 0.290 g / mCPBA / acetonitrile / 1.08 h / -40 - 23 °C

With 1H-tetrazole; sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; sodium methylate; 3-chloro-benzenecarboperoxoic acid; nickel dichloride; In methanol; dichloromethane; acetonitrile;
DOI:10.1002/1521-3765(20021004)8:19<4424::AID-CHEM4424>3.0.CO;2-1

Reference yield:

: 154970-29-3
6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl trichloroacetimidate

: 497096-21-6
2-(benzyloxycarbonyl)aminoethyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-dibenzylphosphate-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 54 percent / TMSOTf / CH₂Cl₂ / 0.5 h / 0 °C

2: NaBH₄; NiCl₂*6H₂O / methanol / 1 h / 0 - 10 °C

3: 8.15 g / methanol / 0.5 h / 5 °C

4: 93 percent / NaOMe / methanol / 0.5 h / 23 °C

5: tetrazole / acetonitrile / 0.5 h / 23 °C

6: 0.290 g / mCPBA / acetonitrile / 1.08 h / -40 - 23 °C

With 1H-tetrazole; sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; sodium methylate; 3-chloro-benzenecarboperoxoic acid; nickel dichloride; In methanol; dichloromethane; acetonitrile;
DOI:10.1002/1521-3765(20021004)8:19<4424::AID-CHEM4424>3.0.CO;2-1