(-)-(2S,3R,4R,5S)-2-[2-(tert-butyldiphenylsilyloxy)propyl]tetrahydro-2H-pyran-3,4,5-triol

Base Information

• Chemical Name: (-)-(2S,3R,4R,5S)-2-[2-(tert-butyldiphenylsilyloxy)propyl]tetrahydro-2H-pyran-3,4,5-triol
• CAS No.: 1173008-80-4
• Molecular Formula: C₂₄H₃₄O₅Si
• Molecular Weight: 430.616

Synonyms:(-)-(2S,3R,4R,5S)-2-[2-(tert-butyldiphenylsilyloxy)propyl]tetrahydro-2H-pyran-3,4,5-triol

Chemical Property of (-)-(2S,3R,4R,5S)-2-[2-(tert-butyldiphenylsilyloxy)propyl]tetrahydro-2H-pyran-3,4,5-triol

Chemical Property:

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Technology Process of (-)-(2S,3R,4R,5S)-2-[2-(tert-butyldiphenylsilyloxy)propyl]tetrahydro-2H-pyran-3,4,5-triol

There total 1 articles about (-)-(2S,3R,4R,5S)-2-[2-(tert-butyldiphenylsilyloxy)propyl]tetrahydro-2H-pyran-3,4,5-triol 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: 96.0%

(-)-(3R,6S)-6-[2-(tert-butyldiphenylsilyloxy)propyl]-3,6-dihydro-2H-pyran-3-ol (1173008-81-5) → (-)-(2S,3R,4R,5S)-2-[2-(tert-butyldiphenylsilyloxy)propyl]tetrahydro-2H-pyran-3,4,5-triol (1173008-80-4)

Guidance literature:

With osmium(VIII) oxide; trimethylamine-N-oxide; In water; acetone; at 20 ℃;

DOI:10.1016/j.tetlet.2008.04.107

Reference yield: 86.0%

(-)-(2S,3R,4R,5S)-2-[2-(tert-butyldiphenylsilyloxy)propyl]tetrahydro-2H-pyran-3,4,5-triol (1173008-80-4) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → (-)-(3aS,4S,7S,7aR)-4-[2-(tert-butyldiphenylsilyloxy)propyl]tetrahydro-3aH-spiro[[1,3]dioxolo[4,5-c]pyran-2,1'-cyclohexan]-7-ol (1173008-82-6)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; at 20 ℃;

DOI:10.1016/j.tetlet.2008.04.107

Reference yield: 84.0%

(-)-(2S,3R,4R,5S)-2-[2-(tert-butyldiphenylsilyloxy)propyl]tetrahydro-2H-pyran-3,4,5-triol (1173008-80-4) + 2,2-dimethoxy-propane (77-76-9) → (-)-(3aS,4S,7S,7aR)-4-[2-(tert-butyldiphenylsilyloxy)propyl]-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol (1173009-25-0)

Guidance literature:

With toluene-4-sulfonic acid; at 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1002/ejoc.200801133

upstream raw materials:

(-)-(3R,6S)-6-[2-(tert-butyldiphenylsilyloxy)propyl]-3,6-dihydro-2H-pyran-3-ol

Downstream raw materials:

(-)-(3aS,4S,7S,7aR)-4-[2-(tert-butyldiphenylsilyloxy)propyl]tetrahydro-3aH-spiro[[1,3]dioxolo[4,5-c]pyran-2,1'-cyclohexan]-7-ol

(-)-(3aS,4S,7S,7aR)-4-[2-(tert-butyldiphenylsilyloxy)propyl]-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol

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