(1S,3R,5S) 7-aza-3,5-di-(diphenylmethoxycarbonyl)-2-oxabicyclo<3.2.0>heptan-7-one

Base Information

Chemical Name:(1S,3R,5S) 7-aza-3,5-di-(diphenylmethoxycarbonyl)-2-oxabicyclo<3.2.0>heptan-7-one
CAS No.:141599-21-5
Molecular Formula:C₃₃H₂₇NO₆
Molecular Weight:533.58
Hs Code.:

Synonyms:(1S,3R,5S) 7-aza-3,5-di-(diphenylmethoxycarbonyl)-2-oxabicyclo<3.2.0>heptan-7-one

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Chemical Property of (1S,3R,5S) 7-aza-3,5-di-(diphenylmethoxycarbonyl)-2-oxabicyclo<3.2.0>heptan-7-one

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Technology Process of (1S,3R,5S) 7-aza-3,5-di-(diphenylmethoxycarbonyl)-2-oxabicyclo<3.2.0>heptan-7-one

There total 6 articles about (1S,3R,5S) 7-aza-3,5-di-(diphenylmethoxycarbonyl)-2-oxabicyclo<3.2.0>heptan-7-one 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: 20.0%

: 141599-18-0
(3S,4S,1'R) 1-t-butyldimethylsilyl-3-diphenylmethoxycarbonyl-4-(2'-bromo-1'-diphenylmethoxycarbonyl)ethoxy-azetidinone-2

: 141599-20-4
E 2-diphenylmethoxcarbonylvinyl-1'-diphenylmethoxycarbonylvinyl ether

: 141599-21-5
(1S,3R,5S) 7-aza-3,5-di-(diphenylmethoxycarbonyl)-2-oxabicyclo<3.2.0>heptan-7-one

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -40 ℃; for 0.25h;
DOI:10.1016/S0040-4020(01)90975-5

Reference yield:

: 121250-72-4
3,4,6-tri-O-benzyl-2-carboxy-2-deoxy-α-D-galactohexopyranosylaminolactam

: 141599-21-5
(1S,3R,5S) 7-aza-3,5-di-(diphenylmethoxycarbonyl)-2-oxabicyclo<3.2.0>heptan-7-one

Guidance literature:: Multi-step reaction with 6 steps

1: 86 percent / 4-N,N-dimethylaminopyridine / dimethylformamide / 16 h / Ambient temperature

2: 96 percent / H₂ / 5percent Pd/C / ethyl acetate / 16 h / 760 Torr / Ambient temperature

3: 1) NaIO₄, 2) 35percent hydrogen peroxide, sodium chlorite / 1) t-BuOH, 8percent aq. NH₄H₂PO₄, H₂O, room temperature, 2) H₂O

4: diethyl ether

5: 69 percent / PPh₃, CBr₄, pyridine / 0.67 h / 0 °C

6: 20 percent / Bu₄NF / tetrahydrofuran / 0.25 h / -40 °C

With pyridine; dmap; sodium chlorite; sodium periodate; carbon tetrabromide; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)90975-5

Reference yield:

: 141599-08-8
3,4,6-tri-O-benzyl-N-t-butyldimethylsilyl-2-C:1-N-carbonyl-2-deoxy-α-D-galactopyranosylamine

: 141599-21-5
(1S,3R,5S) 7-aza-3,5-di-(diphenylmethoxycarbonyl)-2-oxabicyclo<3.2.0>heptan-7-one

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / H₂ / 5percent Pd/C / ethyl acetate / 16 h / 760 Torr / Ambient temperature

2: 1) NaIO₄, 2) 35percent hydrogen peroxide, sodium chlorite / 1) t-BuOH, 8percent aq. NH₄H₂PO₄, H₂O, room temperature, 2) H₂O

3: diethyl ether

4: 69 percent / PPh₃, CBr₄, pyridine / 0.67 h / 0 °C

5: 20 percent / Bu₄NF / tetrahydrofuran / 0.25 h / -40 °C

With pyridine; sodium chlorite; sodium periodate; carbon tetrabromide; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethyl acetate;
DOI:10.1016/S0040-4020(01)90975-5