4(S)-(N-Benzyl-N-tert-butyloxycarbonyl)amino-6-benzyloxy-2,3-(2S,3S)-isopropylidenedioxyhexane

Base Information

Chemical Name:4(S)-(N-Benzyl-N-tert-butyloxycarbonyl)amino-6-benzyloxy-2,3-(2S,3S)-isopropylidenedioxyhexane
CAS No.:142545-29-7
Molecular Formula:C₂₈H₃₉NO₅
Molecular Weight:469.621
Hs Code.:

Synonyms:4(S)-(N-Benzyl-N-tert-butyloxycarbonyl)amino-6-benzyloxy-2,3-(2S,3S)-isopropylidenedioxyhexane

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Chemical Property of 4(S)-(N-Benzyl-N-tert-butyloxycarbonyl)amino-6-benzyloxy-2,3-(2S,3S)-isopropylidenedioxyhexane

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Technology Process of 4(S)-(N-Benzyl-N-tert-butyloxycarbonyl)amino-6-benzyloxy-2,3-(2S,3S)-isopropylidenedioxyhexane

There total 12 articles about 4(S)-(N-Benzyl-N-tert-butyloxycarbonyl)amino-6-benzyloxy-2,3-(2S,3S)-isopropylidenedioxyhexane 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: 91.0%

: 142545-32-2
Benzyl-[(1S,2S,3S)-1-(2-benzyloxy-ethyl)-2,3-dihydroxy-butyl]-carbamic acid tert-butyl ester

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

: 142545-29-7
4(S)-(N-Benzyl-N-tert-butyloxycarbonyl)amino-6-benzyloxy-2,3-(2S,3S)-isopropylidenedioxyhexane

Guidance literature:: With toluene-4-sulfonic acid; In acetone; for 0.75h; Ambient temperature;
DOI:10.1016/S0040-4020(01)92199-4

Reference yield:

: 87219-29-2
benzyl (3S)-5-oxotetrahydro-3-furanylcarbamate

: 142545-29-7
4(S)-(N-Benzyl-N-tert-butyloxycarbonyl)amino-6-benzyloxy-2,3-(2S,3S)-isopropylidenedioxyhexane

Guidance literature:: Multi-step reaction with 11 steps

1: 83 percent / dicyclohexylcarbodiimide / 72 h / Ambient temperature

2: 94 percent / imidazole / dimethylformamide / 2 h / 40 °C

3: 98 percent / H₂ / 5percent Pd/C / methanol / 8 h / Ambient temperature

4: 82 percent / LiAlH₄ / diethyl ether / 1) -25 deg C, 2) 0 deg C, 2 h

5: 74 percent / NaH / dimethylformamide / 2 h / Ambient temperature

6: 97 percent / Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

7: 95 percent / SO₃-pyridine, Et₃N / dimethylsulfoxide / 0.25 h / Ambient temperature

8: 81 percent / diethyl ether / 1 h / -78 °C

9: 70 percent / 3-chloroperoxybenzoic acid / CH₂Cl₂ / 96 h / 5 °C

10: 78 percent / i-Bu₂AlH / diethyl ether; toluene / 1.5 h / -40 °C

11: 91 percent / p-TsOH / acetone / 0.75 h / Ambient temperature

With 1H-imidazole; lithium aluminium tetrahydride; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1016/S0040-4020(01)92199-4

Reference yield:

: 192517-47-8
methyl (3S)-3-[[(benzyloxy)carbonyl]amino]-4-hydroxybutanoate

: 142545-29-7
4(S)-(N-Benzyl-N-tert-butyloxycarbonyl)amino-6-benzyloxy-2,3-(2S,3S)-isopropylidenedioxyhexane

Guidance literature:: Multi-step reaction with 10 steps

1: 94 percent / imidazole / dimethylformamide / 2 h / 40 °C

2: 98 percent / H₂ / 5percent Pd/C / methanol / 8 h / Ambient temperature

3: 82 percent / LiAlH₄ / diethyl ether / 1) -25 deg C, 2) 0 deg C, 2 h

4: 74 percent / NaH / dimethylformamide / 2 h / Ambient temperature

5: 97 percent / Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

6: 95 percent / SO₃-pyridine, Et₃N / dimethylsulfoxide / 0.25 h / Ambient temperature

7: 81 percent / diethyl ether / 1 h / -78 °C

8: 70 percent / 3-chloroperoxybenzoic acid / CH₂Cl₂ / 96 h / 5 °C

9: 78 percent / i-Bu₂AlH / diethyl ether; toluene / 1.5 h / -40 °C

10: 91 percent / p-TsOH / acetone / 0.75 h / Ambient temperature

With 1H-imidazole; lithium aluminium tetrahydride; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1016/S0040-4020(01)92199-4