137664-58-5

Basic information

• Product Name: (4R,5R)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid 4-methoxy-benzylamide
• Synonyms: (4R,5R)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid 4-methoxy-benzylamide
• CAS NO: 137664-58-5
• Molecular Weight: 295.335
• Mol File: 137664-58-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (4R,5R)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid 4-methoxy-benzylamide(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,5R)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid 4-methoxy-benzylamide(137664-58-5)
• EPA Substance Registry System: (4R,5R)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid 4-methoxy-benzylamide(137664-58-5)

Safety Data

• Hazardous Substances Data: 137664-58-5(Hazardous Substances Data)

Upstream product

• 25581-41-3 D-erythronolactone acetonide 
• 2393-23-9 4-methoxy-benzylamine 

Downstream Products

• 137664-64-3 [(R)-1-((4R,5R)-5-{(R)-3-[4-(tert-Butyl-diphenyl-silanyloxymethyl)-oxazol-2-yl]-butylcarbamoyl}-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-ethyl]-carbamic acid tert-butyl ester 
• 137664-63-2 (3aR,6R,6aR)-5-(4-Methoxy-benzyl)-6-methoxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one 
• 137664-61-0 (3aR,6R,6aR)-6-(3,3-Dimethyl-2-oxo-butyl)-5-(4-methoxy-benzyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one 
• 137664-66-5 (3aR,6R,6aR)-5-(4-Methoxy-benzoyl)-6-methoxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one 
• 137664-60-9 Acetic acid (3aS,6aR)-5-(4-methoxy-benzyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl ester 
• 137664-62-1 (3aR,6R,6aR)-6-Hydroxymethyl-5-(4-methoxy-benzyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one 
• 137664-59-6 (3aR,6aS)-6-Hydroxy-5-(4-methoxy-benzyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one 

Relevant articles and documents

Total synthesis of (+)-calyculin A and (-)-calyculin B: Cyanotetraene construction, asymmetric synthesis of the C(26-37) oxazole, fragment assembly, and final elaboration

A convergent total synthesis leading to (+)-calyculin A and (-)-calyculin B (1 and 2), antipodes of the potent, highly selective and remarkably cell-permeable phosphatase inhibitors calyculins A and B, has been achieved. In the preceding paper we outlined the asymmetric synthesis of the C(9-25) spiroketal dipropionate subunit (+)-BC; herein we describe construction of the C(1-8) cyanotetraene, an asymmetric synthesis of the C(26-37) oxazole, fragment assembly and final elaboration to (+)-1 and (-)-2. Highlights of the synthesis include: application of a one-pot three-component Suzuki reaction for the construction of phosphonate A, a bifunctional triene precursor of the light sensitive C(1-8) cyanotetraene subunit, an asymmetric synthesis of the C(26-32) oxazole (-)-D, exploiting the Silks-Odom 77Se NMR protocol to assess enantiomeric purity, construction of the C(33-37) subtarget (-)-E in a highly stereocontrolled fashion via an acyliminium ion, and a concise, highly efficient sequence for fragment assembly and elaboration to (+)-calyculin A and (-)-calyculin B. The synthesis of (-)-2 also confirms the structure of calyculin B, previously based only on spectral comparison with calyculin A.