(2R,3R,4S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-(3-trimethylsilanyl-prop-2-ynyl)-tetrahydro-pyran

Base Information

Chemical Name:(2R,3R,4S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-(3-trimethylsilanyl-prop-2-ynyl)-tetrahydro-pyran
CAS No.:370886-95-6
Molecular Formula:C₂₄H₄₀O₃Si₂
Molecular Weight:432.751
Hs Code.:

Synonyms:(2R,3R,4S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-(3-trimethylsilanyl-prop-2-ynyl)-tetrahydro-pyran

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Chemical Property of (2R,3R,4S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-(3-trimethylsilanyl-prop-2-ynyl)-tetrahydro-pyran

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Technology Process of (2R,3R,4S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-(3-trimethylsilanyl-prop-2-ynyl)-tetrahydro-pyran

There total 10 articles about (2R,3R,4S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-(3-trimethylsilanyl-prop-2-ynyl)-tetrahydro-pyran 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:

: 2873-29-2
D-glucal triacetate

: 370886-95-6
(2R,3R,4S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-(3-trimethylsilanyl-prop-2-ynyl)-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 10 steps

1: 100 percent / H₂ / Pd/C / methanol / 20 °C

2: 100 percent / NaoMe / methanol / 20 °C

3: 100 percent / PPTS / dimethylformamide / 20 °C

4: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

5: L-selectride / tetrahydrofuran / -78 °C

6: NaH / dimethylformamide / 0 - 20 °C

7: p-TsOH / methanol / 20 °C

8: 2,6-lutidine / CH₂Cl₂ / -78 °C

9: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

With 2,6-dimethylpyridine; n-butyllithium; oxalyl dichloride; hydrogen; sodium methylate; pyridinium p-toluenesulfonate; L-Selectride; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(01)01067-X

Reference yield:

: 370886-61-6
Trifluoro-methanesulfonic acid (2R,3S,4S)-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester

: 1066-54-2
trimethylsilylacetylene

: 370886-95-6
(2R,3R,4S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-(3-trimethylsilanyl-prop-2-ynyl)-tetrahydro-pyran

Guidance literature:: With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 ℃;
DOI:10.1016/S0040-4039(01)01067-X

Reference yield:

: 370887-48-2
(2R,3S,4S)-4-Benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-ol

: 370886-95-6
(2R,3R,4S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-(3-trimethylsilanyl-prop-2-ynyl)-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 3 steps

1: 2,6-lutidine / CH₂Cl₂ / -78 °C

2: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

With 2,6-dimethylpyridine; n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;
DOI:10.1016/S0040-4039(01)01067-X