methyl 3-azido-4,5,7-tri-O-benzyl-2,3-dideoxy-2-ethylthio-α-D-manno-hept-2-ulopyranosonate

Base Information

Chemical Name:methyl 3-azido-4,5,7-tri-O-benzyl-2,3-dideoxy-2-ethylthio-α-D-manno-hept-2-ulopyranosonate
CAS No.:667917-78-4
Molecular Formula:C₃₁H₃₅N₃O₆S
Molecular Weight:577.701
Hs Code.:

Synonyms:methyl 3-azido-4,5,7-tri-O-benzyl-2,3-dideoxy-2-ethylthio-α-D-manno-hept-2-ulopyranosonate

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Chemical Property of methyl 3-azido-4,5,7-tri-O-benzyl-2,3-dideoxy-2-ethylthio-α-D-manno-hept-2-ulopyranosonate

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Technology Process of methyl 3-azido-4,5,7-tri-O-benzyl-2,3-dideoxy-2-ethylthio-α-D-manno-hept-2-ulopyranosonate

There total 3 articles about methyl 3-azido-4,5,7-tri-O-benzyl-2,3-dideoxy-2-ethylthio-α-D-manno-hept-2-ulopyranosonate 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:

: (2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-3-trifluoromethanesulfonyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

: 667917-78-4
methyl 3-azido-4,5,7-tri-O-benzyl-2,3-dideoxy-2-ethylthio-α-D-manno-hept-2-ulopyranosonate

Guidance literature:: With tetramethylguanidinum azide; In N,N-dimethyl-formamide; at 20 ℃; for 16h;
DOI:10.1021/jo0353029

Reference yield:

: 404377-25-9
methyl 4,5,7-tri-O-benzyl-2-deoxy-D-gluco-hept-2-ulosonate diethyldithioacetal

: 667917-78-4
methyl 3-azido-4,5,7-tri-O-benzyl-2,3-dideoxy-2-ethylthio-α-D-manno-hept-2-ulopyranosonate

Guidance literature:: Multi-step reaction with 3 steps

1: 76 percent / NIS / acetonitrile / 0.5 h / -30 °C

2: pyridine / CH₂Cl₂ / 1 h / 0 °C

3: tetramethylguanidinium azide / dimethylformamide / 16 h / 20 °C

With pyridine; N-iodo-succinimide; tetramethylguanidinum azide; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo0353029

Reference yield:

: 667917-77-3
methyl 4,5,7-tri-O-benzyl-2-deoxy-2-ethylthio-α-D-gluco-hept-2-ulopyranosonate

: 667917-78-4
methyl 3-azido-4,5,7-tri-O-benzyl-2,3-dideoxy-2-ethylthio-α-D-manno-hept-2-ulopyranosonate

Guidance literature:: Multi-step reaction with 2 steps

1: pyridine / CH₂Cl₂ / 1 h / 0 °C

2: tetramethylguanidinium azide / dimethylformamide / 16 h / 20 °C

With pyridine; tetramethylguanidinum azide; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo0353029