(3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-<(R)-1-hydroxymethylethyl>-2-azetidinone

Base Information

Chemical Name:(3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-<(R)-1-hydroxymethylethyl>-2-azetidinone
CAS No.:104362-98-3
Molecular Formula:C₁₆H₂₁NO₅
Molecular Weight:307.346
Hs Code.:

Synonyms:(3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-<(R)-1-hydroxymethylethyl>-2-azetidinone

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Chemical Property of (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-<(R)-1-hydroxymethylethyl>-2-azetidinone

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Technology Process of (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-<(R)-1-hydroxymethylethyl>-2-azetidinone

There total 8 articles about (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-<(R)-1-hydroxymethylethyl>-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: 85.0%

: 104362-90-5
(3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-<(R)-1-tert-butyldimethylsilyloxymethylethyl>-1-(di-p-anisylmethyl)-2-azetidinone

: 104362-98-3
(3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-<(R)-1-hydroxymethylethyl>-2-azetidinone

Guidance literature:: With boron trifluoride diethyl etherate; 1,3-Dimethoxybenzene; In dichloromethane; 1.) RT, 3 h, 2.) reflux, 5 h;
DOI:10.1248/cpb.40.1098

Reference yield:

: 112057-69-9
(3S,4R)-3-[(1'R)-1'-(benzyloxycarbonyloxy)ethyl]-4-[(1'R)-1'-(t-butyldimethylsilyloxymethyl)ethyl]azetidin-2-one

: 104362-98-3
(3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-<(R)-1-hydroxymethylethyl>-2-azetidinone

Guidance literature:: With acetic acid; In tetrahydrofuran; water;

Reference yield:

: 86258-97-1
(3S,4S)-4-carboxy-1-(di-p-anisylmethyl)-3-<(R)-1-hydroxyethyl>-2-azetidinone

: 104362-98-3
(3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-<(R)-1-hydroxymethylethyl>-2-azetidinone

Guidance literature:: Multi-step reaction with 6 steps

1: 100 percent / 98percent aq. H₂SO₄ / 3 h / 65 °C

2: 88 percent / tetrahydrofuran / 1 h / 0 - 5 °C

3: 100 percent / 4-dimethylaminopyridine (DMAP) / CH₂Cl₂ / 12 h / 0 - 20 °C

4: 89 percent / SOCl₂, pyridine / toluene / 5 h / 20 - 30 °C

5: 72 percent / ceric ammonium nitrate (CAN) / acetonitrile; H₂O / 0.5 h / Ambient temperature

6: 1.) boron trifluoride etherate, NaBH₄, 1,5-cyclooctadiene, 2.) 35percent aq. H₂O₂, aq. NaOH / 1.) THF, 3 h, 2.) THF, 40-45 deg C

With pyridine; dmap; sodium hydroxide; sodium tetrahydroborate; thionyl chloride; 1,5-cis,cis-cyclooctadiene; ammonium cerium(IV) nitrate; sulfuric acid; boron trifluoride diethyl etherate; dihydrogen peroxide; In tetrahydrofuran; dichloromethane; water; toluene; acetonitrile;
DOI:10.1248/cpb.40.1098