2-[(3S,4R,5R)-4-[2-(Dimethyl-phenyl-silanyl)-ethyl]-5-hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-1-trimethylsilanyl-propan-2-ol

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Chemical Name:2-[(3S,4R,5R)-4-[2-(Dimethyl-phenyl-silanyl)-ethyl]-5-hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-1-trimethylsilanyl-propan-2-ol
CAS No.:536745-00-3
Molecular Formula:C₂₈H₄₅NO₄SSi₂
Molecular Weight:547.907
Hs Code.:

Synonyms:2-[(3S,4R,5R)-4-[2-(Dimethyl-phenyl-silanyl)-ethyl]-5-hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-1-trimethylsilanyl-propan-2-ol

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Chemical Property of 2-[(3S,4R,5R)-4-[2-(Dimethyl-phenyl-silanyl)-ethyl]-5-hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-1-trimethylsilanyl-propan-2-ol

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Technology Process of 2-[(3S,4R,5R)-4-[2-(Dimethyl-phenyl-silanyl)-ethyl]-5-hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-1-trimethylsilanyl-propan-2-ol

There total 12 articles about 2-[(3S,4R,5R)-4-[2-(Dimethyl-phenyl-silanyl)-ethyl]-5-hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-1-trimethylsilanyl-propan-2-ol 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: 65.0%

: 1822-00-0
trimethylsilylmethyllithium

: 536744-99-7
1-[4-[2-(dimethylphenylsilanyl)ethyl]-5-hydroxymethyl-1-(toluene-4-sulfonyl)pyrrolidin-3-yl]ethanone

: 536745-00-3
2-[(3S,4R,5R)-4-[2-(Dimethyl-phenyl-silanyl)-ethyl]-5-hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-1-trimethylsilanyl-propan-2-ol

Guidance literature:: In tetrahydrofuran; pentane; at -78 ℃; for 5h;
DOI:10.1021/ol034241y DOI:10.1021/ja043097o

Reference yield:

: 286376-23-6
4-methyl-N-(prop-1-yn-1-yl)benzenesulfonamide

: 536745-00-3
2-[(3S,4R,5R)-4-[2-(Dimethyl-phenyl-silanyl)-ethyl]-5-hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-1-trimethylsilanyl-propan-2-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: Ph₃P; diisopropyl azodicarboxylate / tetrahydrofuran / 48 h / 20 °C

2.1: 80 percent / malonic acid; CpRu[(CH₃CN)3]PF₆ / H₂O; acetone / 3 h / 40 °C

3.1: Li / tetrahydrofuran / 4.5 h / 0 °C

3.2: CuCN / tetrahydrofuran / 0.42 h / 0 °C

3.3: 0.82 g / tetrahydrofuran / 5 h / -78 - 0 °C

4.1: 87 percent / DBU / benzene / 7 h / Heating

5.1: 93 percent / formic acid; Pd/C / methanol / 4 h / 20 °C

6.1: 65 percent / B(O-iPr)3; H₂ / Ir(cod)Py(PCy₃)PF₆ / CH₂Cl₂ / 24 h / 103430 Torr

7.1: 65 percent / tetrahydrofuran; pentane / 5 h / -78 °C

With palladium on activated charcoal; formic acid; cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; Triisopropyl borate; malonic acid; di-isopropyl azodicarboxylate; hydrogen; lithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; Crabtree's catalyst; In tetrahydrofuran; methanol; dichloromethane; water; acetone; pentane; benzene; 1.1: Mitsunobu reaction;
DOI:10.1021/ja043097o

Reference yield:

: 536744-92-0
1-benzyloxy-5-(tert-butyldimethylsilanyloxy)pent-3-yn-2-ol

: 536745-00-3
2-[(3S,4R,5R)-4-[2-(Dimethyl-phenyl-silanyl)-ethyl]-5-hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-1-trimethylsilanyl-propan-2-ol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 99 percent / aq. NaHCO₃; TEMPO; KBr / NaOCl / CH₂Cl₂ / 1.5 h

2.1: 85 percent / LiAlH₄; MeOH; (R)-BINOL / tetrahydrofuran / 0.5 h / -100 - -78 °C

3.1: Ph₃P; diisopropyl azodicarboxylate / tetrahydrofuran / 48 h / 20 °C

4.1: 80 percent / malonic acid; CpRu[(CH₃CN)3]PF₆ / H₂O; acetone / 3 h / 40 °C

5.1: Li / tetrahydrofuran / 4.5 h / 0 °C

5.2: CuCN / tetrahydrofuran / 0.42 h / 0 °C

5.3: 0.82 g / tetrahydrofuran / 5 h / -78 - 0 °C

6.1: 87 percent / DBU / benzene / 7 h / Heating

7.1: 93 percent / formic acid; Pd/C / methanol / 4 h / 20 °C

8.1: 65 percent / B(O-iPr)3; H₂ / Ir(cod)Py(PCy₃)PF₆ / CH₂Cl₂ / 24 h / 103430 Torr

9.1: 65 percent / tetrahydrofuran; pentane / 5 h / -78 °C

With methanol; 2,2,6,6-tetramethyl-piperidine-N-oxyl; palladium on activated charcoal; lithium aluminium tetrahydride; formic acid; cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; Triisopropyl borate; malonic acid; di-isopropyl azodicarboxylate; hydrogen; (R)-1,1'-Bi-2-naphthol; lithium; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; potassium bromide; sodium hypochlorite; Crabtree's catalyst; In tetrahydrofuran; methanol; dichloromethane; water; acetone; pentane; benzene; 3.1: Mitsunobu reaction;
DOI:10.1021/ja043097o