(2S,3S,4S,5R)-2-Benzyloxy-3-methyl-5-triisopropylsilanyloxy-tetrahydro-pyran-4-ol

Base Information

• Chemical Name: (2S,3S,4S,5R)-2-Benzyloxy-3-methyl-5-triisopropylsilanyloxy-tetrahydro-pyran-4-ol
• CAS No.: 206124-71-2
• Molecular Formula: C₂₂H₃₈O₄Si
• Molecular Weight: 394.627
• Mol file: 206124-71-2.mol

Synonyms:(2S,3S,4S,5R)-2-Benzyloxy-3-methyl-5-triisopropylsilanyloxy-tetrahydro-pyran-4-ol

Chemical Property of (2S,3S,4S,5R)-2-Benzyloxy-3-methyl-5-triisopropylsilanyloxy-tetrahydro-pyran-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S,5R)-2-Benzyloxy-3-methyl-5-triisopropylsilanyloxy-tetrahydro-pyran-4-ol

There total 3 articles about (2S,3S,4S,5R)-2-Benzyloxy-3-methyl-5-triisopropylsilanyloxy-tetrahydro-pyran-4-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: 48.0%

methyllithium (917-54-4) + ((1R,2S,5R,6S)-2-Benzyloxy-3,7-dioxa-bicyclo[4.1.0]hept-5-yloxy)-triisopropyl-silane (206125-07-7) → (2S,3R,4R,5S)-2-Benzyloxy-4-methyl-5-triisopropylsilanyloxy-tetrahydro-pyran-3-ol + (2S,3S,4S,5R)-2-Benzyloxy-3-methyl-5-triisopropylsilanyloxy-tetrahydro-pyran-4-ol (206124-71-2)

Guidance literature:

With trimethylaluminum; In diethyl ether; hexane; for 4h; Heating;

DOI:10.1016/S0040-4020(98)00120-3

Reference yield:

triisopropylsilyl chloride (13154-24-0) → (2S,3S,4S,5R)-2-Benzyloxy-3-methyl-5-triisopropylsilanyloxy-tetrahydro-pyran-4-ol (206124-71-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / imidazole / dimethylformamide / 4 h / 40 °C

2: 48 percent / Me₃Al / diethyl ether; hexane / 4 h / Heating

With 1H-imidazole; trimethylaluminum; In diethyl ether; hexane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(98)00120-3

Reference yield:

Benzyl 2,3-anhydro-α-D-ribopyranoside (61134-24-5) → (2S,3S,4S,5R)-2-Benzyloxy-3-methyl-5-triisopropylsilanyloxy-tetrahydro-pyran-4-ol (206124-71-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / imidazole / dimethylformamide / 4 h / 40 °C

2: 48 percent / Me₃Al / diethyl ether; hexane / 4 h / Heating

With 1H-imidazole; trimethylaluminum; In diethyl ether; hexane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(98)00120-3

upstream raw materials:

methyllithium

((1R,2S,5R,6S)-2-Benzyloxy-3,7-dioxa-bicyclo[4.1.0]hept-5-yloxy)-triisopropyl-silane

triisopropylsilyl chloride

Benzyl 2,3-anhydro-α-D-ribopyranoside