(2R,3S)-3-Benzyloxy-5-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-pentane-1,2-diol

Base Information

Chemical Name:(2R,3S)-3-Benzyloxy-5-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-pentane-1,2-diol
CAS No.:524706-32-9
Molecular Formula:C₂₃H₄₀O₅Si
Molecular Weight:424.653
Hs Code.:

Synonyms:(2R,3S)-3-Benzyloxy-5-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-pentane-1,2-diol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,3S)-3-Benzyloxy-5-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-pentane-1,2-diol

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (2R,3S)-3-Benzyloxy-5-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-pentane-1,2-diol

There total 12 articles about (2R,3S)-3-Benzyloxy-5-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-pentane-1,2-diol 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:

: {(2R,3S)-2-[(S)-3-Benzyloxy-3-((R)-2-phenyl-[1,3]dioxolan-4-yl)-propyl]-tetrahydro-pyran-3-yloxy}-tert-butyl-dimethyl-silane

: 524706-32-9
(2R,3S)-3-Benzyloxy-5-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-pentane-1,2-diol

Guidance literature:: With hydrogenchloride; In methanol; at 20 ℃; for 0.0833333h; pH=1;
DOI:10.1021/jo0340556

Reference yield:

: 125877-83-0
(2'S,3'S)-3'-(tert-butyldimethylsiloxy)-tetrahydropyran-2'-carbaldehyde

: 524706-32-9
(2R,3S)-3-Benzyloxy-5-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-pentane-1,2-diol

Guidance literature:: Multi-step reaction with 11 steps

1.1: NaH / benzene / 0.5 h / 0 °C

1.2: 8.5 g / benzene / 0.5 h / 0 °C

2.1: 86 percent / DIBAL / diethyl ether; hexane / 0.5 h / 0 °C

3.1: 100 percent / H₂ / PtO₂ / methanol / 20 °C

4.1: Et₃N; SO₃*Py / CH₂Cl₂ / 0 - 20 °C

5.1: NaH / benzene / 0 °C

5.2: benzene / 0 °C

6.1: 3.9 g / DIBAL / diethyl ether; hexane / 0 °C

7.1: 4 Angstroem molecular sieves; Ti(OPr-i)4; (S,S)-(-)-diethyl tartrate / TBHP / CH₂Cl₂ / -20 - 20 °C

7.2: 71 percent / Ti(OPr-i)4 / CH₂Cl₂ / 2 h / 20 °C

8.1: CSA / CH₂Cl₂ / 2 h / 20 °C

9.1: 3.3 g / NaH / CH₂Cl₂; methanol / 1 h / 0 - 20 °C

10.1: NaH; Bu₄NI / tetrahydrofuran / 24 h / 20 °C

11.1: 442 mg / conc. HCl / methanol / 0.08 h / 20 °C / pH 1

With titanium(IV) isopropylate; hydrogenchloride; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; triethylamine; tert.-butylhydroperoxide; platinum(IV) oxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; benzene; 1.2: Wittig-Horner reaction / 5.2: Wittig-Horner reaction / 7.1: Katsuki-Sharpless asymmetric epoxidation;
DOI:10.1021/jo0340556

Reference yield:

: 138750-71-7,125877-82-9
(2'R,3'S)-<3'-(tert-butyldimethylsilyloxy)tetrahydropyran-2'-yl>methanol

: 524706-32-9
(2R,3S)-3-Benzyloxy-5-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-pentane-1,2-diol

Guidance literature:: Multi-step reaction with 12 steps

1.1: Et₃N; SO₃*Py / CH₂Cl₂ / 0 - 20 °C

2.1: NaH / benzene / 0.5 h / 0 °C

2.2: 8.5 g / benzene / 0.5 h / 0 °C

3.1: 86 percent / DIBAL / diethyl ether; hexane / 0.5 h / 0 °C

4.1: 100 percent / H₂ / PtO₂ / methanol / 20 °C

5.1: Et₃N; SO₃*Py / CH₂Cl₂ / 0 - 20 °C

6.1: NaH / benzene / 0 °C

6.2: benzene / 0 °C

7.1: 3.9 g / DIBAL / diethyl ether; hexane / 0 °C

8.1: 4 Angstroem molecular sieves; Ti(OPr-i)4; (S,S)-(-)-diethyl tartrate / TBHP / CH₂Cl₂ / -20 - 20 °C

8.2: 71 percent / Ti(OPr-i)4 / CH₂Cl₂ / 2 h / 20 °C

9.1: CSA / CH₂Cl₂ / 2 h / 20 °C

10.1: 3.3 g / NaH / CH₂Cl₂; methanol / 1 h / 0 - 20 °C

11.1: NaH; Bu₄NI / tetrahydrofuran / 24 h / 20 °C

12.1: 442 mg / conc. HCl / methanol / 0.08 h / 20 °C / pH 1

With titanium(IV) isopropylate; hydrogenchloride; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; triethylamine; tert.-butylhydroperoxide; platinum(IV) oxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; benzene; 2.2: Wittig-Horner reaction / 6.2: Wittig-Horner reaction / 8.1: Katsuki-Sharpless asymmetric epoxidation;
DOI:10.1021/jo0340556