115185-92-7

Basic information

• Product Name: mycalamide A
• Synonyms: mycalamide A
• CAS NO: 115185-92-7
• Molecular Formula: C₂₄H₄₁NO₁₀
• Molecular Weight: 503.585
• Mol File: 115185-92-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 675.2°Cat760mmHg
• Flash Point: 362.2°C
• Appearance: /
• Density: 1.25g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.539
• PKA: 12.32±0.20(Predicted)
• CAS DataBase Reference: mycalamide A(CAS DataBase Reference)
• NIST Chemistry Reference: mycalamide A(115185-92-7)
• EPA Substance Registry System: mycalamide A(115185-92-7)

Safety Data

• Hazardous Substances Data: 115185-92-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C24H41NO10/c1-12-9-24(31-7,35-14(3)13(12)2)19(28)21(29)25-22-18-17(32-11-33-22)20(30-6)23(4,5)16(34-18)8-15(27)10-26/h13-20,22,26-28H,1,8-11H2,2-7H3,(H,25,29)/t13-,14-,15+,16-,17+,18+,19-,20-,22+,24-/m1/s1

Upstream product

• 67-56-1 methanol 
• 855282-34-7 Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-6-((S)-2,3-diacetoxy-propyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester 
• 866220-25-9 Acetic acid (S)-1-acetoxymethyl-2-((4aS,6R,8S,8aR)-4-azido-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-ethyl ester 
• 855282-32-5 Acetic acid (S)-1-acetoxymethyl-2-((4aS,6R,8S,8aR)-4-amino-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-ethyl ester 
• 855282-47-2 (R)-1-((2R,5R,6R)-2-Methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-2-triethylsilanyloxy-ethanol 
• 128271-03-4 (S)-4-((2R,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl)-[1,3]dioxolan-2-one 
• 128271-11-4 (S)-2-(3,4-Dimethoxy-benzyloxy)-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-N-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-acetamide 
• 128271-11-4 (S)-2-(3,4-Dimethoxy-benzyloxy)-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-N-[(4R,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-acetamide 
• 128271-00-1 (2R,3R,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol 
• 185300-82-7 (S)-(3,4-Dimethoxy-benzyloxy)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-acetic acid methyl ester 
• 128271-10-3 7-(3,4-dimethoxybenzyl)pederic acid 
• 128271-04-5 (S)-4-((2R,4S,5R,6S)-5-Benzyloxy-6-dimethoxymethyl-4-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl)-[1,3]dioxolan-2-one 
• 128271-05-6 (S)-4-((4aS,6R,8S,8aR)-4-Hydroxy-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl)-[1,3]dioxolan-2-one 

Downstream Products

• 126908-48-3 Mycalamide A 18-mono-p-bromobenzoate 
• 139962-12-2 Mycalamide A 17,18-di-p-bromobenzoate 
• 126908-49-4 Mycalamide A 7,18-di-p-bromobenzoate 
• 139962-27-9 Mycalamide A tri-p-bromobenzoate 
• 126884-96-6 Mycalamide A 7-mono-p-bromobenzoate 

Relevant articles and documents

Total synthesis of (+)-mycalamide A

A convergent total synthesis of (+)-mycalamide A is described. A Yb(OTf)3-TMSCl catalytic system is used to synthesize a trioxadecalin ring system, which contains the right segment of mycalamide A. In addition, a tetrahydropyran ring, which is

Total synthesis of mycalamide A

This communication describes a concise and efficient total synthesis of mycalamide A by the convergent coupling of pederic acid unit with the mycalamine unit. The left-half, (+)-7-benzoylpederic acid, was synthesized from (2R,3R)-3-methylpent-4-en-2-ol in

Total synthesis of mycalamide A. Further synthetic study of the right half

The right half 5 of mycalamide A (1) was synthesized starting from (R)- or (S)-pantolactone via the Sharpless asymmetric dihydroxylation as the key step. The total synthesis of mycalamide A (1) was accomplished by coupling of the right and left halves.