Cryptophycin D

Base Information

• Chemical Name: Cryptophycin D
• CAS No.: 155645-51-5
• Molecular Formula: C35H44 N2 O7
• Molecular Weight: 604.744
• DSSTox Substance ID: DTXSID101335279
• Wikidata: Q77371275
• Metabolomics Workbench ID: 114028
• ChEMBL ID: CHEMBL267072
• Mol file: 155645-51-5.mol

Synonyms:Cryptophycin D;CHEMBL267072;DTXSID101335279;155645-51-5

Chemical Property of Cryptophycin D

Chemical Property:

• XLogP3: 6.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 604.31485175
• Heavy Atom Count: 44
• Complexity: 995

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Cryptophycin
• Canonical SMILES: CC1CNC(=O)C(NC(=O)C=CCC(OC(=O)C(OC1=O)CC(C)C)C(C)C=CC2=CC=CC=C2)CC3=CC=C(C=C3)OC
• Isomeric SMILES: C[C@@H]1CNC(=O)[C@H](NC(=O)/C=C/C[C@H](OC(=O)[C@@H](OC1=O)CC(C)C)[C@H](C)/C=C/C2=CC=CC=C2)CC3=CC=C(C=C3)OC

Technology Process of Cryptophycin D

There total 67 articles about Cryptophycin D 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: 76.0%

(2S,2'R,1''S,2''R,1''''R)1''-(3'''-{1''''-[(tert-butoxy)carbonyl]-2''''-p-methoxyphenylethylcarbamoyl}allyl)-2''-methyl-4''-phenylbut-3''-enyl 2-[(3'-{[(tert-butoxy)carbonyl]amino}-2'-methylpropionyl)oxy]-4-methylpentanoate (281191-03-5) → Cryptophycin 4 (155645-51-5)

Guidance literature:

(2S,2'R,1''S,2''R,1''''R)1''-(3'''-{1''''-[(tert-butoxy)carbonyl]-2''''-p-methoxyphenylethylcarbamoyl}allyl)-2''-methyl-4''-phenylbut-3''-enyl 2-[(3'-{[(tert-butoxy)carbonyl]amino}-2'-methylpropionyl)oxy]-4-methylpentanoate; With trifluoroacetic acid; at 23 ℃; for 2h;

With 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 23 ℃; for 1h;

With dmap; In benzene; at 23 ℃; for 12h;

DOI:10.1002/ejoc.200300814

Reference yield: 62.0%

(S)-2-((R)-3-Amino-2-methyl-propionyloxy)-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-1-carboxy-2-(4-methoxy-phenyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester (162465-18-1) → Cryptophycin 4 (155645-51-5)

Guidance literature:

With pentafluorophenyl diphenyl-phosphinate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 25 ℃; for 2.5h;

DOI:10.1021/ja00114a011

Reference yield: 48.0%

(S)-2-((R)-3-Amino-2-methyl-propionyloxy)-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-2-(4-methoxy-phenyl)-1-(2,2,2-trichloro-ethoxycarbonyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester → Cryptophycin 4 (155645-51-5)

Guidance literature:

With 2-hydroxypyridin; In toluene; at 20 ℃;

upstream raw materials:

(S)-2-((R)-3-Amino-2-methyl-propionyloxy)-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-1-carboxy-2-(4-methoxy-phenyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester

tert-butyl (5S,6R)-5-[(2S)-2-[(2R)-3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)-propionylamino]-2-methylpropionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate

(2S,2'R,1''S,2''R,1''''R)1''-(3'''-{1''''-[(tert-butoxy)carbonyl]-2''''-p-methoxyphenylethylcarbamoyl}allyl)-2''-methyl-4''-phenylbut-3''-enyl 2-[(3'-{[(tert-butoxy)carbonyl]amino}-2'-methylpropionyl)oxy]-4-methylpentanoate

trans-styrylacetic acid

Refernces

• 1、 Ghosh, Arun K.,Bischoff. "Asymmetric syntheses of potent antitumor macrolides cryptophycin B and arenastatin A". . p. 2131 - 2141. Retrieved 2007/10/03.
• 2、 Christopher, John A.,Kocienski, Philip J.,Kuhl, Alexander,Bell, Richard. "A synthesis of cryptophycin 4 using a planar chiral molybdenum cationic complex". . p. 463 - 466. Retrieved 2007/10/03.