(4S,5R)-5-(tert-butyldimethylsilyloxy)methyl-2,2-dimethyl-4-(1-phenyl(hydroxy)methyl)-1,3-dioxolane

Base Information

• Chemical Name: (4S,5R)-5-(tert-butyldimethylsilyloxy)methyl-2,2-dimethyl-4-(1-phenyl(hydroxy)methyl)-1,3-dioxolane
• CAS No.: 1224587-93-2
• Molecular Formula: C₁₉H₃₂O₄Si
• Molecular Weight: 352.546

Synonyms:(4S,5R)-5-(tert-butyldimethylsilyloxy)methyl-2,2-dimethyl-4-(1-phenyl(hydroxy)methyl)-1,3-dioxolane

Chemical Property of (4S,5R)-5-(tert-butyldimethylsilyloxy)methyl-2,2-dimethyl-4-(1-phenyl(hydroxy)methyl)-1,3-dioxolane

Chemical Property:

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Technology Process of (4S,5R)-5-(tert-butyldimethylsilyloxy)methyl-2,2-dimethyl-4-(1-phenyl(hydroxy)methyl)-1,3-dioxolane

There total 2 articles about (4S,5R)-5-(tert-butyldimethylsilyloxy)methyl-2,2-dimethyl-4-(1-phenyl(hydroxy)methyl)-1,3-dioxolane 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: 84.0%

(4R,5R)-4-benzoyl-5-(tert-butyldimethylsilyloxy)methyl-2,2-dimethyl-1,3-dioxolane (1224587-91-0) → (4S,5R)-5-(tert-butyldimethylsilyloxy)methyl-2,2-dimethyl-4-(1-phenyl(hydroxy)methyl)-1,3-dioxolane (1224587-93-2)

Guidance literature:

(4R,5R)-4-benzoyl-5-(tert-butyldimethylsilyloxy)methyl-2,2-dimethyl-1,3-dioxolane; With L-Selectride; In tetrahydrofuran; dichloromethane; at -78 ℃; for 1.5h;

With methanol; water; dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; dichloromethane; at -78 - 20 ℃; optical yield given as %de; stereoselective reaction;

DOI:10.1016/j.tet.2010.01.107

Reference yield:

(4R,5R)-4-benzoyl-5-(tert-butyldimethylsilyloxy)methyl-2,2-dimethyl-1,3-dioxolane (1224587-91-0) → (4S,5R)-5-(tert-butyldimethylsilyloxy)methyl-2,2-dimethyl-4-(1-phenyl(hydroxy)methyl)-1,3-dioxolane + (4S,5R)-5-(tert-butyldimethylsilyloxy)methyl-2,2-dimethyl-4-(1-phenyl(hydroxy)methyl)-1,3-dioxolane (1224587-93-2)

Guidance literature:

(4R,5R)-4-benzoyl-5-(tert-butyldimethylsilyloxy)methyl-2,2-dimethyl-1,3-dioxolane; With L-Selectride; In tetrahydrofuran; dichloromethane; at 20 ℃;

With methanol; water; dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; dichloromethane; at 20 ℃; optical yield given as %de; stereoselective reaction;

DOI:10.1016/j.tet.2010.01.107

Reference yield:

(4S,5R)-5-(tert-butyldimethylsilyloxy)methyl-2,2-dimethyl-4-(1-phenyl(hydroxy)methyl)-1,3-dioxolane (1224587-93-2) → (1S,2S,3R)-1-phenylbutane-1,2,3,4-tetrol

Guidance literature:

With acetic acid; In water; at 20 ℃; for 18h;

DOI:10.1016/j.tet.2010.01.107

upstream raw materials:

(4R,5R)-4-benzoyl-5-(tert-butyldimethylsilyloxy)methyl-2,2-dimethyl-1,3-dioxolane

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