(R)-4-Benzyl-3-[(R)-2-((R)-1-hydroxy-2-triisopropylsilanyloxy-ethyl)-but-3-enoyl]-oxazolidin-2-one

Base Information

• Chemical Name: (R)-4-Benzyl-3-[(R)-2-((R)-1-hydroxy-2-triisopropylsilanyloxy-ethyl)-but-3-enoyl]-oxazolidin-2-one
• CAS No.: 724765-16-6
• Molecular Formula: C₂₅H₃₉NO₅Si
• Molecular Weight: 461.674

Synonyms:(R)-4-Benzyl-3-[(R)-2-((R)-1-hydroxy-2-triisopropylsilanyloxy-ethyl)-but-3-enoyl]-oxazolidin-2-one

Chemical Property of (R)-4-Benzyl-3-[(R)-2-((R)-1-hydroxy-2-triisopropylsilanyloxy-ethyl)-but-3-enoyl]-oxazolidin-2-one

Chemical Property:

Purity/Quality:

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Technology Process of (R)-4-Benzyl-3-[(R)-2-((R)-1-hydroxy-2-triisopropylsilanyloxy-ethyl)-but-3-enoyl]-oxazolidin-2-one

There total 1 articles about (R)-4-Benzyl-3-[(R)-2-((R)-1-hydroxy-2-triisopropylsilanyloxy-ethyl)-but-3-enoyl]-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:

triisopropylsilyloxy-acetaldehyde (111998-83-5) + (4R)-3-((E)-2-BUTENOYL)-4-(PHENYLMETHYL)-2-OXAZOLIDINONE (151215-01-9) → (R)-4-Benzyl-3-[(R)-2-((R)-1-hydroxy-2-triisopropylsilanyloxy-ethyl)-but-3-enoyl]-oxazolidin-2-one (724765-16-6)

Guidance literature:

With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at -78 - 0 ℃; for 1.33333h;

DOI:10.1002/anie.200453697

Reference yield:

(R)-4-Benzyl-3-[(R)-2-((R)-1-hydroxy-2-triisopropylsilanyloxy-ethyl)-but-3-enoyl]-oxazolidin-2-one (724765-16-6) → (2R,4S,5R,6S)-6-Allyl-2-((S)-5-benzyloxy-2-hydroxy-pentyl)-2-methoxy-5-vinyl-tetrahydro-pyran-4-ol (724765-23-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 3.65 g / Me₃Al / CH₂Cl₂; toluene / 5 h / -10 - 10 °C

2: 92 percent / tetrahydrofuran; diethyl ether / 0.25 h / 0 °C

3: 94 percent / AcOH; Me₄NB(OAc)3H / acetonitrile / 10.5 h / -20 °C

4: camphorsulfonic acid / acetone / 1 h / Heating

5: 1.52 g / TBAF / tetrahydrofuran / 5 h / 23 °C

6: 99 percent / I₂; PPh₃; imidazole / benzene; diethyl ether / 26 h / 23 °C

7: 92 percent / LDA; N,N'-dimethyl-N,N'-propyleneurea / tetrahydrofuran; hexane / 0.5 h / -40 °C

8: Dowex 50X₂-100 ion-exchange resin; H₂O / methanol / 12 h / 23 °C

9: 0.74 g / Et₃N / methanol / 23 °C

10: 89 percent / pyridinium p-toluenesulfonate / methanol / 24 h / 23 °C

With 1H-imidazole; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; Dowex 50X₂-100 ion-exchange resin; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; iodine; trimethylaluminum; pyridinium p-toluenesulfonate; acetic acid; triethylamine; triphenylphosphine; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetone; toluene; acetonitrile; benzene;

DOI:10.1002/anie.200453697

Reference yield:

(R)-4-Benzyl-3-[(R)-2-((R)-1-hydroxy-2-triisopropylsilanyloxy-ethyl)-but-3-enoyl]-oxazolidin-2-one (724765-16-6) → (2R,4S,5R,6S)-6-Allyl-2-((S)-5-benzyloxy-2-hydroxy-pentyl)-5-vinyl-tetrahydro-pyran-2,4-diol (724765-10-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 3.65 g / Me₃Al / CH₂Cl₂; toluene / 5 h / -10 - 10 °C

2: 92 percent / tetrahydrofuran; diethyl ether / 0.25 h / 0 °C

3: 94 percent / AcOH; Me₄NB(OAc)3H / acetonitrile / 10.5 h / -20 °C

4: camphorsulfonic acid / acetone / 1 h / Heating

5: 1.52 g / TBAF / tetrahydrofuran / 5 h / 23 °C

6: 99 percent / I₂; PPh₃; imidazole / benzene; diethyl ether / 26 h / 23 °C

7: 92 percent / LDA; N,N'-dimethyl-N,N'-propyleneurea / tetrahydrofuran; hexane / 0.5 h / -40 °C

8: Dowex 50X₂-100 ion-exchange resin; H₂O / methanol / 12 h / 23 °C

9: 0.74 g / Et₃N / methanol / 23 °C

With 1H-imidazole; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; Dowex 50X₂-100 ion-exchange resin; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; iodine; trimethylaluminum; acetic acid; triethylamine; triphenylphosphine; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetone; toluene; acetonitrile; benzene;

DOI:10.1002/anie.200453697

upstream raw materials:

triisopropylsilyloxy-acetaldehyde

(4R)-3-((E)-2-BUTENOYL)-4-(PHENYLMETHYL)-2-OXAZOLIDINONE

Downstream raw materials:

(2R,4S,5R,6S)-6-Allyl-2-((S)-5-benzyloxy-2-hydroxy-pentyl)-2-methoxy-5-vinyl-tetrahydro-pyran-4-ol

(2R,4S,5R,6S)-6-Allyl-2-((S)-5-benzyloxy-2-hydroxy-pentyl)-5-vinyl-tetrahydro-pyran-2,4-diol

(4S,6S)-4-((4S,5S,6S)-6-Allyl-2,2-dimethyl-5-vinyl-[1,3]dioxan-4-ylmethyl)-6-(3-benzyloxy-propyl)-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

(2R,4S,5S,6S)-6-Allyl-2-[(S)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-pentyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-vinyl-tetrahydro-pyran

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