(1S,3S,7S,8S)-N-benzyloxycarbonyl-5,5-dimethyl-11-aza-2,4,6-trioxatricyclo<6.4.0.0^3,7>dodecane

Base Information

• Chemical Name: (1S,3S,7S,8S)-N-benzyloxycarbonyl-5,5-dimethyl-11-aza-2,4,6-trioxatricyclo<6.4.0.0^3,7>dodecane
• CAS No.: 123165-55-9
• Molecular Formula: C₁₈H₂₃NO₅
• Molecular Weight: 333.384

Synonyms:(1S,3S,7S,8S)-N-benzyloxycarbonyl-5,5-dimethyl-11-aza-2,4,6-trioxatricyclo<6.4.0.0^3,7>dodecane

Chemical Property of (1S,3S,7S,8S)-N-benzyloxycarbonyl-5,5-dimethyl-11-aza-2,4,6-trioxatricyclo<6.4.0.0^3,7>dodecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S,7S,8S)-N-benzyloxycarbonyl-5,5-dimethyl-11-aza-2,4,6-trioxatricyclo<6.4.0.0^3,7>dodecane

There total 15 articles about (1S,3S,7S,8S)-N-benzyloxycarbonyl-5,5-dimethyl-11-aza-2,4,6-trioxatricyclo<6.4.0.0^3,7>dodecane 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:

5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-β-D-threo-pentofuranose-3-ulose (172751-32-5) → (1S,3S,7S,8S)-N-benzyloxycarbonyl-5,5-dimethyl-11-aza-2,4,6-trioxatricyclo<6.4.0.03,7>dodecane (123165-55-9)

Guidance literature:

Multi-step reaction with 10 steps

1: benzene / 4 h / Heating

2: H₂ / 10percent Pd/C / ethyl acetate / 48 h / Ambient temperature

3: 88 percent / LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature

4: 98 percent / pyridine / 3 h / 0 °C

5: 96 percent / NaN₃ / dimethylformamide / 6 h / 50 °C

6: 95 percent / Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

7: 94 percent / pyridine / 3 h / 0 °C

8: H₂ / Pd black / ethanol / Ambient temperature

9: NaOAc / ethanol / 10 h / Heating

10: aq. NaHCO₃ / ethyl acetate / 0 °C

With lithium aluminium tetrahydride; sodium azide; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; sodium hydrogencarbonate; palladium on activated charcoal; palladium; In tetrahydrofuran; pyridine; ethanol; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1016/0040-4020(94)01009-O

Reference yield:

(3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (114738-04-4) → (1S,3S,7S,8S)-N-benzyloxycarbonyl-5,5-dimethyl-11-aza-2,4,6-trioxatricyclo<6.4.0.03,7>dodecane (123165-55-9)

Guidance literature:

Multi-step reaction with 11 steps

1: pyridinium perchlorate, 3A molecular sieve / CH₂Cl₂ / 4 h / Ambient temperature

2: benzene / 4 h / Heating

3: H₂ / 10percent Pd/C / ethyl acetate / 48 h / Ambient temperature

4: 88 percent / LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature

5: 98 percent / pyridine / 3 h / 0 °C

6: 96 percent / NaN₃ / dimethylformamide / 6 h / 50 °C

7: 95 percent / Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

8: 94 percent / pyridine / 3 h / 0 °C

9: H₂ / Pd black / ethanol / Ambient temperature

10: NaOAc / ethanol / 10 h / Heating

11: aq. NaHCO₃ / ethyl acetate / 0 °C

With lithium aluminium tetrahydride; sodium azide; 3 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; pyridinium perchlorate; sodium hydrogencarbonate; palladium on activated charcoal; palladium; In tetrahydrofuran; pyridine; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1016/0040-4020(94)01009-O

Reference yield:

5-O-(tert-butyldiphenylsilyl)-3-C-(2'-hydroxyethyl)-3-deoxy-1,2-O-isopropylidene-β-D-lyxofuranose (162517-92-2) → (1S,3S,7S,8S)-N-benzyloxycarbonyl-5,5-dimethyl-11-aza-2,4,6-trioxatricyclo<6.4.0.03,7>dodecane (123165-55-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 98 percent / pyridine / 3 h / 0 °C

2: 96 percent / NaN₃ / dimethylformamide / 6 h / 50 °C

3: 95 percent / Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

4: 94 percent / pyridine / 3 h / 0 °C

5: H₂ / Pd black / ethanol / Ambient temperature

6: NaOAc / ethanol / 10 h / Heating

7: aq. NaHCO₃ / ethyl acetate / 0 °C

With sodium azide; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; sodium hydrogencarbonate; palladium; In tetrahydrofuran; pyridine; ethanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/0040-4020(94)01009-O

upstream raw materials:

benzyl chloroformate

D-arabinose diethyl dithioacetal

5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-β-D-threo-pentofuranose-3-ulose

(3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

Downstream raw materials:

(3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-((S)-1,2-dihydroxyethyl)piperidine

(1'S,3S,4S)-N-benzyloxycarbonyl-3-benzyloxy-4-(1'-benzyloxy-2'-hydroxy)ethyl piperidine

(1'S,3S,4S)-N-benzyloxycarbonyl-3-benzyloxy-4-(2',2'-bisthioethyl-1'-benzyloxy)ethyl piperidine

(1'S,3S,4S)-N-benzyloxycarbonyl-3-benzyloxy-4-(1'-benzyloxy-2'-hydroxy-2'-O-methanesulphonyl)ethyl piperidine

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