2(R)-methoxy-4(S)-<(tert-butyldiphenylsilyl)oxy>-2,3-dihydro-4H-pyran

Base Information

• Chemical Name: 2(R)-methoxy-4(S)-<(tert-butyldiphenylsilyl)oxy>-2,3-dihydro-4H-pyran
• CAS No.: 158718-95-7
• Molecular Formula: C₂₂H₂₈O₃Si
• Molecular Weight: 368.548
• Mol file: 158718-95-7.mol

Synonyms:2(R)-methoxy-4(S)-<(tert-butyldiphenylsilyl)oxy>-2,3-dihydro-4H-pyran

Chemical Property of 2(R)-methoxy-4(S)-<(tert-butyldiphenylsilyl)oxy>-2,3-dihydro-4H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2(R)-methoxy-4(S)-<(tert-butyldiphenylsilyl)oxy>-2,3-dihydro-4H-pyran

There total 4 articles about 2(R)-methoxy-4(S)-<(tert-butyldiphenylsilyl)oxy>-2,3-dihydro-4H-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: 53.0%

Trifluoro-methanesulfonic acid (3R,4S,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-3-yl ester → 2(R)-methoxy-4(S)-<(tert-butyldiphenylsilyl)oxy>-2,3-dihydro-4H-pyran (158718-95-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 23 ℃; for 0.5h;

DOI:10.1021/ja00091a004

Reference yield:

(3R,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-3-ol (158719-05-2) → 2(R)-methoxy-4(S)-<(tert-butyldiphenylsilyl)oxy>-2,3-dihydro-4H-pyran (158718-95-7)

Guidance literature:

With trifluoromethylsulfonic anhydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; Multistep reaction; 1.) C₅H₅N, CH₂Cl₂, 0 deg C, 2 h; 2.) 23 deg C, 10 h;

DOI:10.1016/S0040-4039(00)73170-4

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 2(R)-methoxy-4(S)-<(tert-butyldiphenylsilyl)oxy>-2,3-dihydro-4H-pyran (158718-95-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / pyridine, AgNO₃ / tetrahydrofuran / 3 h / 23 °C

2: 97 percent / pyridine / CH₂Cl₂ / 2 h / -20 °C

3: 53 percent / DBU / 0.5 h / 23 °C

With pyridine; silver nitrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00091a004

upstream raw materials:

(3R,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-3-ol

tert-butylchlorodiphenylsilane

methyl 2-deoxy-β-D-erythro-pentopyranoside

Downstream raw materials:

2(R)-methoxy-4(S)-<(tert-butyldiphenylsilyl)oxy>-6-<7(R)-<(tert-butyldiphenylsilyl)oxy>-3(E),5(E),9(Z)-pentadecatrien-1-ynyl>-2,3-dihydro-4H-pyran

tert-Butyl-((2R,4R)-2-methoxy-tetrahydro-pyran-4-yloxy)-diphenyl-silane

3(R),12(R)-bis<(tert-butyldiphenylsilyl)oxy>-5(S)-hydroxy-6(Z),8(E),10(E),14(Z)-eicosatetranoic δ-lactone

2(R)-methoxy-4(R)-<(tert-butyldiphenylsilyl)oxy>-6(S)-<7(R)-<(tert-butyldiphenylsilyl)oxy>-1(Z),3(E),5(E),9(Z)-pentadecatetraen-1-yl>tetrahydropyran