methyl 3-O-benzyl-5-(N-benzyl-N-benzoxycarbonylamino)-5,6,7-trideoxy-1,2-O-isopropylidene-β-L-ido-octo-1,4-furanuronate

Base Information

Chemical Name:methyl 3-O-benzyl-5-(N-benzyl-N-benzoxycarbonylamino)-5,6,7-trideoxy-1,2-O-isopropylidene-β-L-ido-octo-1,4-furanuronate
CAS No.:329361-89-9
Molecular Formula:C₃₄H₃₉NO₈
Molecular Weight:589.686
Hs Code.:

Synonyms:methyl 3-O-benzyl-5-(N-benzyl-N-benzoxycarbonylamino)-5,6,7-trideoxy-1,2-O-isopropylidene-β-L-ido-octo-1,4-furanuronate

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Chemical Property of methyl 3-O-benzyl-5-(N-benzyl-N-benzoxycarbonylamino)-5,6,7-trideoxy-1,2-O-isopropylidene-β-L-ido-octo-1,4-furanuronate

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Technology Process of methyl 3-O-benzyl-5-(N-benzyl-N-benzoxycarbonylamino)-5,6,7-trideoxy-1,2-O-isopropylidene-β-L-ido-octo-1,4-furanuronate

There total 7 articles about methyl 3-O-benzyl-5-(N-benzyl-N-benzoxycarbonylamino)-5,6,7-trideoxy-1,2-O-isopropylidene-β-L-ido-octo-1,4-furanuronate 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: 85.0%

: 67-56-1
methanol

: 329361-90-2
5,6,8-trideoxy-1,2-O-isopropylidene-3-O-benzyl-5-(N-benzyl-N-benzoxycarbonylamino)-8-diazo-β-L-ido-octo-1,4-furan-7-ulose

: 329361-89-9
methyl 3-O-benzyl-5-(N-benzyl-N-benzoxycarbonylamino)-5,6,7-trideoxy-1,2-O-isopropylidene-β-L-ido-octo-1,4-furanuronate

Guidance literature:: With silver benzoate; triethylamine; at 25 ℃; for 1.5h;
DOI:10.1021/jo0010476

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 329361-89-9
methyl 3-O-benzyl-5-(N-benzyl-N-benzoxycarbonylamino)-5,6,7-trideoxy-1,2-O-isopropylidene-β-L-ido-octo-1,4-furanuronate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 97 percent / NaHCO₃ / ethanol; H₂O / 3 h / 30 °C

2.1: 96 percent / LiOH*H₂O / methanol; H₂O / 0 - 25 °C

3.1: Et₃N; ethylchloroformate / tetrahydrofuran / 0.5 h / 0 °C

3.2: 65 percent / diethyl ether / 1.5 h / 0 - 25 °C

4.1: 85 percent / PhCOOAg; Et₃N / 1.5 h / 25 °C

With lithium hydroxide; silver benzoate; chloroformic acid ethyl ester; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; methanol; ethanol; water;
DOI:10.1021/jo0010476

Reference yield:

: 100-46-9
benzylamine

: 329361-89-9
methyl 3-O-benzyl-5-(N-benzyl-N-benzoxycarbonylamino)-5,6,7-trideoxy-1,2-O-isopropylidene-β-L-ido-octo-1,4-furanuronate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 85 percent / tetrahydrofuran / 2 h / -40 °C

2.1: 97 percent / NaHCO₃ / ethanol; H₂O / 3 h / 30 °C

3.1: 96 percent / LiOH*H₂O / methanol; H₂O / 0 - 25 °C

4.1: Et₃N; ethylchloroformate / tetrahydrofuran / 0.5 h / 0 °C

4.2: 65 percent / diethyl ether / 1.5 h / 0 - 25 °C

5.1: 85 percent / PhCOOAg; Et₃N / 1.5 h / 25 °C

With lithium hydroxide; silver benzoate; chloroformic acid ethyl ester; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; methanol; ethanol; water; 1.1: Michael addition;
DOI:10.1021/jo0010476