5-O-acetyl-2-<(benzyloxycarbonyl)amino>-2,3-dideoxy-D-threo-pentonic acid γ-lactone

Base Information

Chemical Name:5-O-acetyl-2-<(benzyloxycarbonyl)amino>-2,3-dideoxy-D-threo-pentonic acid γ-lactone
CAS No.:97551-66-1
Molecular Formula:C₁₅H₁₇NO₆
Molecular Weight:307.303
Hs Code.:

Synonyms:5-O-acetyl-2-<(benzyloxycarbonyl)amino>-2,3-dideoxy-D-threo-pentonic acid γ-lactone

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Chemical Property of 5-O-acetyl-2-<(benzyloxycarbonyl)amino>-2,3-dideoxy-D-threo-pentonic acid γ-lactone

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Technology Process of 5-O-acetyl-2-<(benzyloxycarbonyl)amino>-2,3-dideoxy-D-threo-pentonic acid γ-lactone

There total 9 articles about 5-O-acetyl-2-<(benzyloxycarbonyl)amino>-2,3-dideoxy-D-threo-pentonic acid γ-lactone 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: 90.5%

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

: 97551-65-0
5-O-acetyl-2-amino-2,3-dideoxy-D-threo-pentonic acid γ-lactone hydrochloride

: 97551-66-1
5-O-acetyl-2-<(benzyloxycarbonyl)amino>-2,3-dideoxy-D-threo-pentonic acid γ-lactone

Guidance literature:: With sodium hydrogencarbonate; In diethyl ether; water; at 4 - 20 ℃; for 2.5h;
DOI:10.1021/jo00219a008

Reference yield:

: 80244-96-8
5-O-acetyl-1,2-O-isopropylidene-α-D-xylofuranose

: 97551-66-1
5-O-acetyl-2-<(benzyloxycarbonyl)amino>-2,3-dideoxy-D-threo-pentonic acid γ-lactone

Guidance literature:: Multi-step reaction with 8 steps

1: 97.3 percent / 1,2-dichloro-ethane / 1 h / Heating

2: 95 percent / Bu3SnH, α,α'-azobis(isobutyronitrile) (AIBN) / toluene / 1 h / Heating

3: 60.9 percent / trifluoroacetic acid (TFA) / 1.25 h / 5 °C

4: 1.) dibutyltin oxide, 2.) Et₃N / 1.) MeOH, reflux, 1.5 h, 2.) 1,2-dimethoxyethane, 4 deg C, 1 h

5: 98 percent / RuO₄ / 1,2-dichloro-ethane / 1 h / 4 - 20 °C

6: 90.1 percent / LiN₃ / dimethylformamide / Ambient temperature

7: 51 percent / H₂, HCl / 10percent Pd/C / ethanol / 0.75 h / 760 Torr

8: 90.5 percent / NaHCO₃ / H₂O; diethyl ether / 2.5 h / 4 - 20 °C

With hydrogenchloride; ruthenium tetroxide; lithium azide; azobisisobutyronitrile; hydrogen; tri-n-butyl-tin hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In diethyl ether; ethanol; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00219a008

Reference yield:

: 20031-21-4
1,2-O-isopropylidene-α-D-xylose

: 97551-66-1
5-O-acetyl-2-<(benzyloxycarbonyl)amino>-2,3-dideoxy-D-threo-pentonic acid γ-lactone

Guidance literature:: Multi-step reaction with 9 steps

1: 85.1 percent / pyridine / CH₂Cl₂ / Ambient temperature

2: 97.3 percent / 1,2-dichloro-ethane / 1 h / Heating

3: 95 percent / Bu3SnH, α,α'-azobis(isobutyronitrile) (AIBN) / toluene / 1 h / Heating

4: 60.9 percent / trifluoroacetic acid (TFA) / 1.25 h / 5 °C

5: 1.) dibutyltin oxide, 2.) Et₃N / 1.) MeOH, reflux, 1.5 h, 2.) 1,2-dimethoxyethane, 4 deg C, 1 h

6: 98 percent / RuO₄ / 1,2-dichloro-ethane / 1 h / 4 - 20 °C

7: 90.1 percent / LiN₃ / dimethylformamide / Ambient temperature

8: 51 percent / H₂, HCl / 10percent Pd/C / ethanol / 0.75 h / 760 Torr

9: 90.5 percent / NaHCO₃ / H₂O; diethyl ether / 2.5 h / 4 - 20 °C

With pyridine; hydrogenchloride; ruthenium tetroxide; lithium azide; azobisisobutyronitrile; hydrogen; tri-n-butyl-tin hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In diethyl ether; ethanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00219a008