ethyl 4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-mannopyranoside

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Chemical Name:ethyl 4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-mannopyranoside
CAS No.:884844-08-0
Molecular Formula:C₂₄H₂₉N₃O₅S
Molecular Weight:471.577
Hs Code.:

Synonyms:ethyl 4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-mannopyranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of ethyl 4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-mannopyranoside

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Technology Process of ethyl 4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-mannopyranoside

There total 8 articles about ethyl 4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-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: 89.0%

: 884844-07-9
ethyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-mannopyranoside

: 108-24-7
acetic anhydride

: 884844-08-0
ethyl 4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-mannopyranoside

Guidance literature:: With pyridine; at 20 ℃;
DOI:10.1055/s-2006-926297

Reference yield:

: 141810-60-8
ethyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

: 884844-08-0
ethyl 4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-mannopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 84 percent / pyridine / 0 - 20 °C

2: 82 percent / LiN₃ / dimethylformamide / 16 h / 80 °C

3: AlCl₃; BH₃*Et₃N; 4 Angstroem molecular sieves / diethyl ether; CH₂Cl₂ / 1 h / 0 °C

4: 89 percent / pyridine / 20 °C

With pyridine; aluminium trichloride; lithium azide; triethylamine-borane; 4 A molecular sieve; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1055/s-2006-926297

Reference yield:

: 39686-94-7,56632-47-4,65827-58-9,99202-62-7,99202-66-1,103082-79-7,103703-00-0,103703-01-1,118711-49-2,127853-23-0,139563-66-9
1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose

: 884844-08-0
ethyl 4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-mannopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 79 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂ / 2 h / 0 °C

2: 72 percent / NaOMe / methanol / 144 h / 20 °C

3: 84 percent / TfOH / CH₂Cl₂ / 1 h

4: 84 percent / pyridine / 0 - 20 °C

5: 82 percent / LiN₃ / dimethylformamide / 16 h / 80 °C

6: AlCl₃; BH₃*Et₃N; 4 Angstroem molecular sieves / diethyl ether; CH₂Cl₂ / 1 h / 0 °C

7: 89 percent / pyridine / 20 °C

With pyridine; aluminium trichloride; lithium azide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; triethylamine-borane; 4 A molecular sieve; sodium methylate; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1055/s-2006-926297