(4S,5R)-5-((S)-hydroxy(phenyl)methyl)-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide

Base Information

• Chemical Name: (4S,5R)-5-((S)-hydroxy(phenyl)methyl)-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide
• CAS No.: 887927-67-5
• Molecular Formula: C₁₅H₂₁NO₄
• Molecular Weight: 279.336
• Mol file: 887927-67-5.mol

Synonyms:(4S,5R)-5-((S)-hydroxy(phenyl)methyl)-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide

Chemical Property of (4S,5R)-5-((S)-hydroxy(phenyl)methyl)-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-5-((S)-hydroxy(phenyl)methyl)-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide

There total 4 articles about (4S,5R)-5-((S)-hydroxy(phenyl)methyl)-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide 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: 86.0%

(4S,5S)-5-benzoyl-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide (868761-55-1) → (4S,5R)-5-((S)-hydroxy(phenyl)methyl)-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide (887927-67-5)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at -78 ℃; for 2h;

DOI:10.1021/jo0702342

Reference yield: 86.0%

(4S,5S)-5-benzoyl-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide (868761-55-1) → (4S,5R)-5-((R)-hydroxy(phenyl)methyl)-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide + (4S,5R)-5-((S)-hydroxy(phenyl)methyl)-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide (887927-67-5)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at -78 ℃; for 1.5h;

DOI:10.1021/jo060159f

Reference yield:

(S,S)-(-)-N,N,N',N'-tetramethyl-2,2-dimethyl-1,3-dioxolane-trans-4,5-dicarboxamide (111828-49-0,74752-95-7) → (4S,5R)-5-((S)-hydroxy(phenyl)methyl)-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide (887927-67-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / tetrahydrofuran / 0.5 h / -10 - -5 °C

2: 86 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 1.5 h / -78 °C

With sodium tetrahydroborate; cerium(III) chloride; In tetrahydrofuran; methanol;

DOI:10.1021/jo060159f

upstream raw materials:

(4S,5S)-5-benzoyl-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide

(S,S)-(-)-N,N,N',N'-tetramethyl-2,2-dimethyl-1,3-dioxolane-trans-4,5-dicarboxamide

Downstream raw materials:

(2S,3R,4S)-methyl 2,3,4-trihydroxy-4-phenylbutanoate

1-(S)-((4S,5R)-5-((S)-tert-butyldimethylsilyloxy(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-enyl 4-methylbenzenesulfonate

(S)-((4S,5R)-5-((S)-1-(methoxymethoxy)pent-4-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methyl 4-methylbenzenesulfonate

(2S,3S,4S,5R)-2-(but-3-enyl)-3,4-bis-tert-butyldimethylsilyloxy-tetrahydro-5-phenylfuran