(R)-4-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-benzyloxymethyl-oxazolidin-2-one

Base Information

Chemical Name:(R)-4-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-benzyloxymethyl-oxazolidin-2-one
CAS No.:148236-85-5
Molecular Formula:C₂₅H₂₉NO₇
Molecular Weight:455.508
Hs Code.:

Synonyms:

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Chemical Property of (R)-4-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-benzyloxymethyl-oxazolidin-2-one

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Technology Process of (R)-4-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-benzyloxymethyl-oxazolidin-2-one

There total 8 articles about (R)-4-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-benzyloxymethyl-oxazolidin-2-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:

: 22529-61-9
(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

: 148236-85-5
(R)-4-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-benzyloxymethyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: imidazole / dimethylformamide / 4 h / Ambient temperature

2: 1.) oxalyl chloride, DMSO, 2.) Et₃N / -78 deg C, 2 h

3: 80 percent / tetrahydrofuran / 1 h / Ambient temperature

4: Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

5: PPh₃, diethyl azodicarboxylate / toluene / 5 h / Heating

6: 76 percent / triisopropyl phosphite / Pd(PPh)3 / tetrahydrofuran / 18 h / Ambient temperature

7: 1.) O₃, NaBH₄, 2.) NaH / 1.) CH₂Cl₂, 2.) THF, 5 h

8: CAN / acetonitrile; H₂O / 6 h / Ambient temperature

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; ammonium cerium(IV) nitrate; triisopropyl phosphite; tetrabutyl ammonium fluoride; sodium hydride; ozone; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/0040-4039(93)85033-S

Reference yield:

: 106445-04-9
1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethanol

: 148236-85-5
(R)-4-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-benzyloxymethyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) oxalyl chloride, DMSO, 2.) Et₃N / -78 deg C, 2 h

2: 80 percent / tetrahydrofuran / 1 h / Ambient temperature

3: Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

4: PPh₃, diethyl azodicarboxylate / toluene / 5 h / Heating

5: 76 percent / triisopropyl phosphite / Pd(PPh)3 / tetrahydrofuran / 18 h / Ambient temperature

6: 1.) O₃, NaBH₄, 2.) NaH / 1.) CH₂Cl₂, 2.) THF, 5 h

7: CAN / acetonitrile; H₂O / 6 h / Ambient temperature

With sodium tetrahydroborate; oxalyl dichloride; ammonium cerium(IV) nitrate; triisopropyl phosphite; tetrabutyl ammonium fluoride; sodium hydride; ozone; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; water; toluene; acetonitrile;
DOI:10.1016/0040-4039(93)85033-S

Reference yield:

: 106445-05-0
3-O-benzyl-6-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D-xylo-hexofuran-5-ulose

: 148236-85-5
(R)-4-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-benzyloxymethyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 80 percent / tetrahydrofuran / 1 h / Ambient temperature

2: Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

3: PPh₃, diethyl azodicarboxylate / toluene / 5 h / Heating

4: 76 percent / triisopropyl phosphite / Pd(PPh)3 / tetrahydrofuran / 18 h / Ambient temperature

5: 1.) O₃, NaBH₄, 2.) NaH / 1.) CH₂Cl₂, 2.) THF, 5 h

6: CAN / acetonitrile; H₂O / 6 h / Ambient temperature

With sodium tetrahydroborate; ammonium cerium(IV) nitrate; triisopropyl phosphite; tetrabutyl ammonium fluoride; sodium hydride; ozone; triphenylphosphine; diethylazodicarboxylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; water; toluene; acetonitrile;
DOI:10.1016/0040-4039(93)85033-S