2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-1,6-anhydro-β-D-mannopyranose

Base Information

Chemical Name:2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-1,6-anhydro-β-D-mannopyranose
CAS No.:334834-26-3
Molecular Formula:C₂₇H₂₅NO₉
Molecular Weight:507.497
Hs Code.:

Synonyms:2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-1,6-anhydro-β-D-mannopyranose

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Chemical Property of 2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-1,6-anhydro-β-D-mannopyranose

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Technology Process of 2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-1,6-anhydro-β-D-mannopyranose

There total 1 articles about 2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-1,6-anhydro-β-D-mannopyranose 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: 75.0%

: 86861-42-9
1,6-anhydro-2,4-di-O-benzyl-β-D-mannopyranose

: 7693-46-1
4-Nitrophenyl chloroformate

: 334834-26-3
2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-1,6-anhydro-β-D-mannopyranose

Guidance literature:: With dmap; triethylamine; In tetrahydrofuran; at 20 ℃; for 12h;
DOI:10.1021/ja003508a

Reference yield: 88.0%

: 108-24-7
acetic anhydride

: 334834-26-3
2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-1,6-anhydro-β-D-mannopyranose

: 334834-27-4
6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl acetate

Guidance literature:: With trifluoroacetic acid; at 20 ℃; for 10h;
DOI:10.1021/ja003508a

Reference yield:

: 334834-26-3
2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-1,6-anhydro-β-D-mannopyranose

: 2-O-{6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl}-6-O-acetyl-4-O-benzoyl-3-O-benzyl-L-gulopyranosyl acetate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 88 percent / TFA / 10 h / 20 °C

2.1: 94 percent / 30percent HBr; AcOH / 8 h

3.1: DBMP / CH₂Cl₂ / 1 h / -15 °C

3.2: 78 percent / AgOTf / CH₂Cl₂ / -15 - 20 °C

4.1: 87 percent / TFA / 48 h

With 2,6-di-tert-butyl-4-methyl-phenol; acetic acid; trifluoroacetic acid; In dichloromethane;
DOI:10.1021/ja003508a