1-benzyl-3-<(S)-4,5-dihydro-5-<(trityloxy)methyl>-2-furyl>-3-hydroxy-2-azetidinone

Base Information

Chemical Name:1-benzyl-3-<(S)-4,5-dihydro-5-<(trityloxy)methyl>-2-furyl>-3-hydroxy-2-azetidinone
CAS No.:205495-53-0
Molecular Formula:C₃₄H₃₁NO₄
Molecular Weight:517.624
Hs Code.:

Synonyms:1-benzyl-3-<(S)-4,5-dihydro-5-<(trityloxy)methyl>-2-furyl>-3-hydroxy-2-azetidinone

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Chemical Property of 1-benzyl-3-<(S)-4,5-dihydro-5-<(trityloxy)methyl>-2-furyl>-3-hydroxy-2-azetidinone

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Technology Process of 1-benzyl-3-<(S)-4,5-dihydro-5-<(trityloxy)methyl>-2-furyl>-3-hydroxy-2-azetidinone

There total 7 articles about 1-benzyl-3-<(S)-4,5-dihydro-5-<(trityloxy)methyl>-2-furyl>-3-hydroxy-2-azetidinone 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: 58.0%

: 75986-07-1
N-benzylazetidine-2,3-dione

: Tributyl-((S)-5-trityloxymethyl-4,5-dihydro-furan-2-yl)-stannane

: 205495-53-0
1-benzyl-3-<(S)-4,5-dihydro-5-<(trityloxy)methyl>-2-furyl>-3-hydroxy-2-azetidinone

Guidance literature:: With n-butyllithium; boron trifluoride diethyl etherate; 1.) -78 deg C;
DOI:10.3987/com-97-s6

Reference yield:

: 32780-06-6
(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

: 205495-53-0
1-benzyl-3-<(S)-4,5-dihydro-5-<(trityloxy)methyl>-2-furyl>-3-hydroxy-2-azetidinone

Guidance literature:: Multi-step reaction with 5 steps

1: DMAP, Et₃N

2: Dibal-H / CH₂Cl₂; diethyl ether

3: 74 percent / pyridine

4: 91 percent / 1.5 h / 190 °C / 0.5 Torr / Heating

5: 1.) t-BuLi, 2.) BF₃*OEt₂ / 1.) THF, pentane, -78 deg C, 1 h, 2.) THF, pentane, ether, -78 deg C, 30 min, then -10 deg C, 30 min

With dmap; boron trifluoride diethyl etherate; tert.-butyl lithium; diisobutylaluminium hydride; triethylamine; In pyridine; diethyl ether; dichloromethane;
DOI:10.1021/jo982259u

Reference yield:

: 76-83-5
trityl chloride

: 205495-53-0
1-benzyl-3-<(S)-4,5-dihydro-5-<(trityloxy)methyl>-2-furyl>-3-hydroxy-2-azetidinone

Guidance literature:: Multi-step reaction with 5 steps

1: DMAP, Et₃N

2: Dibal-H / CH₂Cl₂; diethyl ether

3: 74 percent / pyridine

4: 91 percent / 1.5 h / 190 °C / 0.5 Torr / Heating

5: 1.) t-BuLi, 2.) BF₃*OEt₂ / 1.) THF, pentane, -78 deg C, 1 h, 2.) THF, pentane, ether, -78 deg C, 30 min, then -10 deg C, 30 min

With dmap; boron trifluoride diethyl etherate; tert.-butyl lithium; diisobutylaluminium hydride; triethylamine; In pyridine; diethyl ether; dichloromethane;
DOI:10.1021/jo982259u