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

Base Information

• Chemical Name: ((2R,3R,4S)-4-Benzyloxy-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane
• CAS No.: 370886-63-8
• Molecular Formula: C₂₁H₃₂O₃Si
• Molecular Weight: 360.569
• Mol file: 370886-63-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about ((2R,3R,4S)-4-Benzyloxy-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane 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: 100.0%

(2R,3R,4S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-(3-trimethylsilanyl-prop-2-ynyl)-tetrahydro-pyran (370886-95-6) → ((2R,3R,4S)-4-Benzyloxy-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane (370886-63-8)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃;

DOI:10.1016/S0040-4039(01)01067-X

Reference yield:

D-glucal triacetate (2873-29-2) → ((2R,3R,4S)-4-Benzyloxy-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane (370886-63-8)

Guidance literature:

Multi-step reaction with 11 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

10: 100 percent / K₂CO₃ / methanol / 20 °C

With 2,6-dimethylpyridine; n-butyllithium; oxalyl dichloride; hydrogen; sodium methylate; pyridinium p-toluenesulfonate; L-Selectride; sodium hydride; potassium carbonate; 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:

(2R,3S,4S)-4-Benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-ol (370887-48-2) → ((2R,3R,4S)-4-Benzyloxy-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane (370886-63-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 2,6-lutidine / CH₂Cl₂ / -78 °C

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

3: 100 percent / K₂CO₃ / methanol / 20 °C

With 2,6-dimethylpyridine; n-butyllithium; potassium carbonate; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

DOI:10.1016/S0040-4039(01)01067-X

upstream raw materials:

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

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

1,2-dideoxy-4,6-O-isopropylidine-D-glucopyranose

(3S,4R)-dihydroxy-(2R)-(hydroxymethyl)tetrahydropyran

Downstream raw materials:

(2R,4aR,8S,8aS,2'R,4'S,4'aR,6'R,7'R,8'aR)-8,7'-Bis-benzyloxy-6'-benzyloxymethyl-4'-chloro-2-hydroxy-dodecahydro-[2,2']bi[pyrano[3,2-b]pyranyl]-3-one

(2S,3S,4aR,8S,8aS,2'R,4'S,4'aR,6'R,7'R,8'aR)-8,7'-Bis-benzyloxy-6'-benzyloxymethyl-4'-chloro-dodecahydro-[2,2']bi[pyrano[3,2-b]pyranyl]-2,3-diol

{(2R,3R,4S)-4-Benzyloxy-2-[(Z)-3-((2R,4S,4aR,6R,7R,8aR)-7-benzyloxy-6-benzyloxymethyl-4-chloro-octahydro-pyrano[3,2-b]pyran-2-yl)-allyl]-tetrahydro-pyran-3-yloxy}-tert-butyl-dimethyl-silane

(2R,4R,4aS,6R,7R,8aR)-7-Benzyloxy-2-{(Z)-3-[(2R,3R,4S)-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-propenyl}-6-benzyloxymethyl-octahydro-pyrano[3,2-b]pyran-4-ol