(3-acetamido-4,5,7-tri-O-benzyl-3-deoxy-2-O-methyl-α-D-mannno-hept-2-ulopyranos-1-yl) dibenzyl phosphate

Base Information

Chemical Name:(3-acetamido-4,5,7-tri-O-benzyl-3-deoxy-2-O-methyl-α-D-mannno-hept-2-ulopyranos-1-yl) dibenzyl phosphate
CAS No.:667917-95-5
Molecular Formula:C₄₅H₅₀NO₁₀P
Molecular Weight:795.866
Hs Code.:

Synonyms:(3-acetamido-4,5,7-tri-O-benzyl-3-deoxy-2-O-methyl-α-D-mannno-hept-2-ulopyranos-1-yl) dibenzyl phosphate

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Chemical Property of (3-acetamido-4,5,7-tri-O-benzyl-3-deoxy-2-O-methyl-α-D-mannno-hept-2-ulopyranos-1-yl) dibenzyl phosphate

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Technology Process of (3-acetamido-4,5,7-tri-O-benzyl-3-deoxy-2-O-methyl-α-D-mannno-hept-2-ulopyranos-1-yl) dibenzyl phosphate

There total 11 articles about (3-acetamido-4,5,7-tri-O-benzyl-3-deoxy-2-O-methyl-α-D-mannno-hept-2-ulopyranos-1-yl) dibenzyl phosphate 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:

: Phosphorous acid (2R,3S,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-2-ylmethyl ester dibenzyl ester

: 667917-95-5
(3-acetamido-4,5,7-tri-O-benzyl-3-deoxy-2-O-methyl-α-D-mannno-hept-2-ulopyranos-1-yl) dibenzyl phosphate

Guidance literature:: With tert.-butylhydroperoxide; In decane; dichloromethane; at 20 ℃;
DOI:10.1021/jo0353029

Reference yield:

: 404377-35-1
methyl 3-O-acetyl-4,5,7-tri-O-benzyl-α-D-gluco-hept-2-ulopyranosonate

: 667917-95-5
(3-acetamido-4,5,7-tri-O-benzyl-3-deoxy-2-O-methyl-α-D-mannno-hept-2-ulopyranos-1-yl) dibenzyl phosphate

Guidance literature:: Multi-step reaction with 9 steps

1: NaH / dimethylformamide / 2 h / 20 °C

2: NaOMe / dimethylformamide; methanol / 16 h / 20 °C

3: pyridine / CH₂Cl₂ / 2 h / 0 - 15 °C

4: tetramethylguanidinium azide / dimethylformamide / 48 h / 60 °C

5: pyridine; H₂S / H₂O / 16 h / 20 °C

6: pyridine / 20 h / 20 °C

7: 81 percent / NaBH₄ / tetrahydrofuran; ethanol / 20 h / 20 °C

8: 1H-tetrazole / CH₂Cl₂ / 5 h

9: tert-butyl hydroperoxide / CH₂Cl₂; decane / 20 °C

With pyridine; 1H-tetrazole; tert.-butylhydroperoxide; sodium tetrahydroborate; hydrogen sulfide; sodium methylate; sodium hydride; tetramethylguanidinum azide; In tetrahydrofuran; methanol; decane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo0353029

Reference yield:

: 667917-81-9
methyl 3-azido-4,5,7-tri-O-benzyl-3-deoxy-α-D-manno-hept-2-ulopyranosonate

: 667917-95-5
(3-acetamido-4,5,7-tri-O-benzyl-3-deoxy-2-O-methyl-α-D-mannno-hept-2-ulopyranos-1-yl) dibenzyl phosphate

Guidance literature:: Multi-step reaction with 6 steps

1: 87 percent / NaH / dimethylformamide / 2 h / 20 °C

2: pyridine; H₂S / H₂O / 16 h / 20 °C

3: pyridine / 20 h / 20 °C

4: 81 percent / NaBH₄ / tetrahydrofuran; ethanol / 20 h / 20 °C

5: 1H-tetrazole / CH₂Cl₂ / 5 h

6: tert-butyl hydroperoxide / CH₂Cl₂; decane / 20 °C

With pyridine; 1H-tetrazole; tert.-butylhydroperoxide; sodium tetrahydroborate; hydrogen sulfide; sodium hydride; In tetrahydrofuran; decane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo0353029