(2S,3S,4S)-2,3-(isopropylidene)dioxy-4-(N-tert-butoxycarbonyl)amino-5-cyanopentanoic acid

Base Information

Chemical Name:(2S,3S,4S)-2,3-(isopropylidene)dioxy-4-(N-tert-butoxycarbonyl)amino-5-cyanopentanoic acid
CAS No.:118868-05-6
Molecular Formula:C₁₄H₂₂N₂O₆
Molecular Weight:314.338
Hs Code.:

Synonyms:(2S,3S,4S)-2,3-(isopropylidene)dioxy-4-(N-tert-butoxycarbonyl)amino-5-cyanopentanoic acid

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Chemical Property of (2S,3S,4S)-2,3-(isopropylidene)dioxy-4-(N-tert-butoxycarbonyl)amino-5-cyanopentanoic acid

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Technology Process of (2S,3S,4S)-2,3-(isopropylidene)dioxy-4-(N-tert-butoxycarbonyl)amino-5-cyanopentanoic acid

There total 1 articles about (2S,3S,4S)-2,3-(isopropylidene)dioxy-4-(N-tert-butoxycarbonyl)amino-5-cyanopentanoic acid 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:

: 68766-96-1
ethyl (R)-2-pyrrolidone-5-carboxylate

: 118868-05-6
(2S,3S,4S)-2,3-(isopropylidene)dioxy-4-(N-tert-butoxycarbonyl)amino-5-cyanopentanoic acid

Guidance literature:: Multi-step reaction with 10 steps

1: 79 percent / sodium borohydride / ethanol / 2 h / Ambient temperature

2: 72 percent / p-toluenesulfonic acid, molecular sieves 4 A / toluene / Heating

3: 1) butyllithium, diisopropylamine / 1) hexane, THF,-70 deg C, 30 min, 2) THF, 15 min

4: 1) ozone, 2) pyridine / 1) CH₂Cl₂, -74 deg C, 2 h, 2) -74 deg C up to room temp.

5: 65 percent / OsO₄, N-methylmorpholine N-oxide / H₂O; acetone; 2-methyl-propan-2-ol / 15 h / Ambient temperature

6: 98 percent / PPTS / acetone / 10 h / Ambient temperature

7: 95 percent / methanol / 0.5 h / Heating

8: 95 percent / 18-crown-6, tri-n-butyl phosphine, CCl₄ / acetonitrile / 1a) 30-40 deg C, 1 h, 1b) 70-80 deg C, 2 h

9: 92 percent / DMAP / acetonitrile / 1 h / Ambient temperature

10: 70 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 0.5 h / Ambient temperature

With pyridine; tetrachloromethane; lithium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; 18-crown-6 ether; tributylphosphine; 4 A molecular sieve; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; ozone; 4-methylmorpholine N-oxide; diisopropylamine; dmap; In tetrahydrofuran; methanol; ethanol; water; acetone; toluene; acetonitrile; tert-butyl alcohol;
DOI:10.1016/S0040-4020(01)82406-6

Reference yield:

: 118868-05-6
(2S,3S,4S)-2,3-(isopropylidene)dioxy-4-(N-tert-butoxycarbonyl)amino-5-cyanopentanoic acid

: 124665-87-8
(3S,4S₅S)-3-(benzyloxycarbonyl)amino-5-ethoxycarbonyl-5-hydroxy-4-pentanolide

Guidance literature:: Multi-step reaction with 2 steps

1: HCl gas / 0 deg C, 5 min, r.t., 11 h 78percent

2: 75 percent / NaHCO₃ / H₂O; ethyl acetate / 6 h / 0 °C

With hydrogenchloride; sodium hydrogencarbonate; In water; ethyl acetate;

Reference yield:

: 118868-05-6
(2S,3S,4S)-2,3-(isopropylidene)dioxy-4-(N-tert-butoxycarbonyl)amino-5-cyanopentanoic acid

: 77674-99-8
6-<<1(S)-<3(S),4-dihydro-8-hydroxy-1-oxo-1H-2-benzopyran-3-yl>-3-methylbutyl>amino>-4(S),5(S)-dihydroxy-6-oxo-3(S)-ammoniohexanoate

Guidance literature:: Multi-step reaction with 3 steps

1: 70 percent / diethyl phosphorocyanidate, triethylamine / dimethylformamide / 1.) 0 deg C, 3 h, 2.) room temp., 31 h

2: 5percent hydrogen chloride-MeOH, trimethyl orthoformate / 44.5 h / 5 °C

3: 1.) H₂O, 2.) 0.1 N NaOH / 1.) 12 h, 2.) aq. MeOH, room temp., 3 h

With hydrogenchloride; sodium hydroxide; diethyl cyanophosphonate; water; triethylamine; trimethyl orthoformate; In N,N-dimethyl-formamide;
DOI:10.1021/ja00186a071