(2R,3R,4S)-2-((R)-1-Hydroxy-2-trityloxy-ethyl)-4-methoxy-5,5-dimethyl-tetrahydro-pyran-3-ol

Base Information

Chemical Name:(2R,3R,4S)-2-((R)-1-Hydroxy-2-trityloxy-ethyl)-4-methoxy-5,5-dimethyl-tetrahydro-pyran-3-ol
CAS No.:152998-22-6
Molecular Formula:C₂₉H₃₄O₅
Molecular Weight:462.586
Hs Code.:

Synonyms:(2R,3R,4S)-2-((R)-1-Hydroxy-2-trityloxy-ethyl)-4-methoxy-5,5-dimethyl-tetrahydro-pyran-3-ol

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Chemical Property of (2R,3R,4S)-2-((R)-1-Hydroxy-2-trityloxy-ethyl)-4-methoxy-5,5-dimethyl-tetrahydro-pyran-3-ol

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Technology Process of (2R,3R,4S)-2-((R)-1-Hydroxy-2-trityloxy-ethyl)-4-methoxy-5,5-dimethyl-tetrahydro-pyran-3-ol

There total 10 articles about (2R,3R,4S)-2-((R)-1-Hydroxy-2-trityloxy-ethyl)-4-methoxy-5,5-dimethyl-tetrahydro-pyran-3-ol 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: 85.0%

: 76-83-5
trityl chloride

: 152998-21-5
(R)-1-((2R,3R,4S)-3-Hydroxy-4-methoxy-5,5-dimethyl-tetrahydro-pyran-2-yl)-ethane-1,2-diol

: 152998-22-6
(2R,3R,4S)-2-((R)-1-Hydroxy-2-trityloxy-ethyl)-4-methoxy-5,5-dimethyl-tetrahydro-pyran-3-ol

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 23 ℃;
DOI:10.1016/S0040-4039(00)73924-4

Reference yield:

: 152998-15-7
(S)-3-((R)-2,2-Diethyl-[1,3]dioxolan-4-yl)-3-methoxy-2,2-dimethyl-propan-1-ol

: 152998-22-6
(2R,3R,4S)-2-((R)-1-Hydroxy-2-trityloxy-ethyl)-4-methoxy-5,5-dimethyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 8 steps

1: 86 percent / imidazole / dimethylformamide / 60 °C

2: HCO₂H / methanol / 23 °C

3: 78 percent / NaIO₄ / tetrahydrofuran; H₂O / 23 °C

4: 86 percent / 4A mol. sieves / toluene / -78 °C

5: 1.) dimethyldioxirane, K₂CO₃ / 1.) acetone, 23 deg C; 2.) MeOH, HOAc

6: 92 percent / Ti(O-i-Pr)4, (-)-DIPT, (i-Pr)2NEt / CH₂Cl₂ / -20 °C

7: 86 percent / HF / acetonitrile / Ambient temperature

8: 85 percent / (i-Pr)2NEt / CH₂Cl₂ / 23 °C

With 1H-imidazole; titanium(IV) isopropylate; sodium periodate; formic acid; 4 A molecular sieve; hydrogen fluoride; 3,3-dimethyldioxirane; potassium carbonate; D-(-)-diisopropyl tartrate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0040-4039(00)73924-4

Reference yield:

: 152998-13-5
(S)-1-((R)-2,2-Diethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-but-3-en-1-ol

: 152998-22-6
(2R,3R,4S)-2-((R)-1-Hydroxy-2-trityloxy-ethyl)-4-methoxy-5,5-dimethyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 10 steps

1: 93 percent / NaH / dimethylformamide / 23 °C

2: 1.) O₃; 2.) NaBH₄ / 1.) -78 deg C, CH₂Cl₂-MeOH; 2.) EtOH

3: 86 percent / imidazole / dimethylformamide / 60 °C

4: HCO₂H / methanol / 23 °C

5: 78 percent / NaIO₄ / tetrahydrofuran; H₂O / 23 °C

6: 86 percent / 4A mol. sieves / toluene / -78 °C

7: 1.) dimethyldioxirane, K₂CO₃ / 1.) acetone, 23 deg C; 2.) MeOH, HOAc

8: 92 percent / Ti(O-i-Pr)4, (-)-DIPT, (i-Pr)2NEt / CH₂Cl₂ / -20 °C

9: 86 percent / HF / acetonitrile / Ambient temperature

10: 85 percent / (i-Pr)2NEt / CH₂Cl₂ / 23 °C

With 1H-imidazole; titanium(IV) isopropylate; sodium tetrahydroborate; sodium periodate; formic acid; 4 A molecular sieve; hydrogen fluoride; 3,3-dimethyldioxirane; sodium hydride; potassium carbonate; D-(-)-diisopropyl tartrate; ozone; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0040-4039(00)73924-4