4S,5S,-2-(N-benzyloxycarbonyl)amino-5,6-dihydroxy-5,6-O-isopropylidene-hex-2-en-4-olide

Base Information

Chemical Name:4S,5S,-2-(N-benzyloxycarbonyl)amino-5,6-dihydroxy-5,6-O-isopropylidene-hex-2-en-4-olide
CAS No.:111651-97-9
Molecular Formula:C₁₇H₁₉NO₆
Molecular Weight:333.341
Hs Code.:

Synonyms:4S,5S,-2-(N-benzyloxycarbonyl)amino-5,6-dihydroxy-5,6-O-isopropylidene-hex-2-en-4-olide

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Chemical Property of 4S,5S,-2-(N-benzyloxycarbonyl)amino-5,6-dihydroxy-5,6-O-isopropylidene-hex-2-en-4-olide

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Technology Process of 4S,5S,-2-(N-benzyloxycarbonyl)amino-5,6-dihydroxy-5,6-O-isopropylidene-hex-2-en-4-olide

There total 2 articles about 4S,5S,-2-(N-benzyloxycarbonyl)amino-5,6-dihydroxy-5,6-O-isopropylidene-hex-2-en-4-olide 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: 95.0%

: 108428-45-1
4S,5S-2-(N-benzyloxycarbonyl)amino-5,6-dihydroxyhex-2-en-4-olide

: 77-76-9
2,2-dimethoxy-propane

: 111651-97-9
4S,5S,-2-(N-benzyloxycarbonyl)amino-5,6-dihydroxy-5,6-O-isopropylidene-hex-2-en-4-olide

Guidance literature:: With toluene-4-sulfonic acid; at 20 ℃; for 30h;
DOI:10.1016/S0040-4020(01)89973-7

Reference yield:

: 43139-78-2
5-(N-benzyloxycarbonyl)amino-5-deoxy-1,2-O-isopropylidene-β-L-iduronolactone

: 111651-97-9
4S,5S,-2-(N-benzyloxycarbonyl)amino-5,6-dihydroxy-5,6-O-isopropylidene-hex-2-en-4-olide

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) sodium methoxide; 2.) sodium borohydride / 1.) methanol, -10 deg C, 2 min.; 2.) 0 deg C, 10 min.

2: 95 percent / toluenesulphonic acid / 30 h / 20 °C

With sodium tetrahydroborate; sodium methylate; toluene-4-sulfonic acid;
DOI:10.1016/S0040-4020(01)89973-7

Reference yield:

: 111651-97-9
4S,5S,-2-(N-benzyloxycarbonyl)amino-5,6-dihydroxy-5,6-O-isopropylidene-hex-2-en-4-olide

: 111651-99-1
2S,4S,5S-2-(N-benzyloxycarbonyl)amino-5,6-dihydroxy-5,6-O-isopropylidene-hexan-4-olide

Guidance literature:: Multi-step reaction with 2 steps

1: 97 percent / H₂ / Pd / ethyl acetate / 24 h / Ambient temperature

2: sodium bicarbonate sat. / H₂O / 0.25 h / 0 °C

With hydrogen; sodium hydrogencarbonate; palladium; In water; ethyl acetate;
DOI:10.1016/S0040-4020(01)89973-7