(1S,2R)-1-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methoxy-3-phenyl-propan-2-ol

Base Information

• Chemical Name: (1S,2R)-1-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methoxy-3-phenyl-propan-2-ol
• CAS No.: 264891-48-7
• Molecular Formula: C₁₆H₂₄O₅
• Molecular Weight: 296.364
• Mol file: 264891-48-7.mol

Synonyms:(1S,2R)-1-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methoxy-3-phenyl-propan-2-ol

Chemical Property of (1S,2R)-1-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methoxy-3-phenyl-propan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R)-1-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methoxy-3-phenyl-propan-2-ol

There total 1 articles about (1S,2R)-1-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methoxy-3-phenyl-propan-2-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: 56.0%

phenylmagnesium bromide (1589-82-8) + (3aS,7R,7aS)-7-Methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ol → (1S,2R)-1-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methoxy-3-phenyl-propan-2-ol (264891-48-7) + (1S,2S)-1-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methoxy-3-phenyl-propan-2-ol

Guidance literature:

In tetrahydrofuran; at 0 ℃;

DOI:10.1016/S0040-4039(99)02177-2

Reference yield: 48.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (1S,2R)-1-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methoxy-3-phenyl-propan-2-ol (264891-48-7) → (1S,2R)-1-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-1-methoxy-3-phenyl-propan-2-ol (264891-52-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 25 ℃;

DOI:10.1016/S0040-4039(99)02177-2

Reference yield:

(1S,2R)-1-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methoxy-3-phenyl-propan-2-ol (264891-48-7) → (1R,2S)-1-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methoxy-2-methyl-3-phenyl-propan-2-ol

Guidance literature:

Multi-step reaction with 4 steps

1: 48 percent / imidazole / dimethylformamide / 25 °C

2: 96 percent / PCC; molecular sieves 4 Angstroem / CH₂Cl₂ / 25 °C

3: 76 percent / tetrahydrofuran / 0 °C

4: Bu₄NF / tetrahydrofuran / 25 °C

With 1H-imidazole; 4 A molecular sieve; tetrabutyl ammonium fluoride; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Alkylation / 2: Oxidation / 3: Alkylation / 4: desilylation;

DOI:10.1016/S0040-4039(99)02177-2

upstream raw materials:

phenylmagnesium bromide

Downstream raw materials:

(1S,2R)-1-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-1-methoxy-3-phenyl-propan-2-ol

(3aR,6S,7R,7aR)-6-Benzyl-7-methoxy-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-one

(R)-1-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-1-methoxy-3-phenyl-propan-2-one

(1R,2S)-1-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-1-methoxy-2-methyl-3-phenyl-propan-2-ol