N-[3-Hydroxy-1-(5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-triisopropylsilyloxypropyl]-4-methylbenzenesulfonamide

Base Information

Chemical Name:N-[3-Hydroxy-1-(5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-triisopropylsilyloxypropyl]-4-methylbenzenesulfonamide
CAS No.:253778-02-8
Molecular Formula:C₂₅H₄₅NO₇SSi
Molecular Weight:531.786
Hs Code.:

Synonyms:N-[3-Hydroxy-1-(5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-triisopropylsilyloxypropyl]-4-methylbenzenesulfonamide

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Chemical Property of N-[3-Hydroxy-1-(5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-triisopropylsilyloxypropyl]-4-methylbenzenesulfonamide

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Technology Process of N-[3-Hydroxy-1-(5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-triisopropylsilyloxypropyl]-4-methylbenzenesulfonamide

There total 1 articles about N-[3-Hydroxy-1-(5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-triisopropylsilyloxypropyl]-4-methylbenzenesulfonamide 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: 62.0%

: 253778-01-7
N-(5-Triisopropylsilyloxy-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[1,3]dioxol-4-yl)-4-methylbenzenesulfonamide

: 253778-02-8
N-[3-Hydroxy-1-(5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-triisopropylsilyloxypropyl]-4-methylbenzenesulfonamide

Guidance literature:: N-(5-Triisopropylsilyloxy-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[1,3]dioxol-4-yl)-4-methylbenzenesulfonamide; With ozone; In dichloromethane; at -78 ℃; for 0.25h;

With dimethylsulfide; In tetrahydrofuran; at -78 - 20 ℃; for 1h;

With sodium tetrahydroborate; In methanol; at 0 ℃; for 1h;
DOI:10.1002/(SICI)1521-3765(19991105)5:11<3279::AID-CHEM3279>3.0.CO;2-4

Reference yield: 86.0%

: 253778-02-8
N-[3-Hydroxy-1-(5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-triisopropylsilyloxypropyl]-4-methylbenzenesulfonamide

: 253778-03-9
2-[2,2-Dimethyl-5-(toluene-4-sulfonyl)tetrahydro[1,3]dioxolo[4,5-c]pyrrol-4-yl]-2-triisopropylsilyloxyethanol

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 ℃; for 0.75h;
DOI:10.1002/(SICI)1521-3765(19991105)5:11<3279::AID-CHEM3279>3.0.CO;2-4

Reference yield:

: 253778-02-8
N-[3-Hydroxy-1-(5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-triisopropylsilyloxypropyl]-4-methylbenzenesulfonamide

: 72741-87-8
swainsonine

Guidance literature:: Multi-step reaction with 7 steps

1: 86 percent / PPh₃; DIAD / tetrahydrofuran / 0.75 h / 0 °C

2: 98 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.75 h / 20 °C

3: 90 percent / LiCl; DBU / acetonitrile / 2 h / 20 °C

4: 99 percent / H₂ / PtO₂ / ethanol / 1.5 h / 20 °C / 760 Torr

5: 72 percent / Na(Hg); Na₂HPO₄ / methanol / 3 h / 20 °C

6: 95 percent / BH₃*Me₂S / tetrahydrofuran / 2.5 h / 0 - 20 °C

7: 88 percent / HCl; H₂O / tetrahydrofuran / 14 h / 20 °C

With hydrogenchloride; disodium hydrogenphosphate; sodium amalgam; di-isopropyl azodicarboxylate; dimethylsulfide borane complex; water; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; lithium chloride; platinum(IV) oxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetonitrile; 1: Cyclization / 2: Oxidation / 3: Condensation / 4: Catalytic hydrogenation / 5: Cyclization / 6: Reduction / 7: Hydrolysis;
DOI:10.1002/(SICI)1521-3765(19991105)5:11<3279::AID-CHEM3279>3.0.CO;2-4