845521-44-0

Basic information

• Product Name: L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-L-valyl-L-threonyl-O-(phenylmethyl)-, (1S,2S,3R)-1-[(1S)-2-hydroxy-1-methylethyl]-2-methyl-3-(phenylmethoxy )hexadecyl ester
• CAS NO: 845521-44-0
• Molecular Formula: C51H83N3O10
• Molecular Weight: 898.234
• Mol File: 845521-44-0.mol

Chemical Properties

• CAS DataBase Reference: L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-L-valyl-L-threonyl-O-(phenylmethyl)-, (1S,2S,3R)-1-[(1S)-2-hydroxy-1-methylethyl]-2-methyl-3-(phenylmethoxy )hexadecyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-L-valyl-L-threonyl-O-(phenylmethyl)-, (1S,2S,3R)-1-[(1S)-2-hydroxy-1-methylethyl]-2-methyl-3-(phenylmethoxy )hexadecyl ester(845521-44-0)
• EPA Substance Registry System: L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-L-valyl-L-threonyl-O-(phenylmethyl)-, (1S,2S,3R)-1-[(1S)-2-hydroxy-1-methylethyl]-2-methyl-3-(phenylmethoxy )hexadecyl ester(845521-44-0)

Safety Data

• Hazardous Substances Data: 845521-44-0(Hazardous Substances Data)

Upstream product

• 906800-25-7 (4S,5S)-4-((1S,2R)-2-Benzyloxy-1-methyl-pentadecyl)-2,2,5-trimethyl-[1,3]dioxane 
• 467224-46-0 (2S,3R)-2-((4S,5S)-2,2,5-Trimethyl-[1,3]dioxan-4-yl)-hexadecan-3-ol 
• 100-39-0 benzyl bromide 
• 845521-41-7 (2S,3S,4R,5R)-2,4-dimethyl-5-(phenylmethoxy)-1-[(triethylsilyl)oxy]-3-octadecanol 
• 845521-40-6 (2S,3S,4R,5R)-5-Benzyloxy-2,4-dimethyl-octadecane-1,3-diol 
• 467224-45-9 (2S,3S,4S,5R)-3-methoxy-2,4-dimethyl-1,5-octadecanediol 
• 467224-43-7 1,6-bis-O-(2,2-dimethylpropanoyl)-2,4-dideoxy-2,4-dimethyl-5-O-methylsulfonyl-3-O-methyl-L-mannitol 
• 467224-51-7 1,6-bis-O-(2,2-dimethylpropanoyl)-2,4-dideoxy-2,4-dimethyl-3-O-methyl-L-mannitol 
• 467224-44-8 1,2-anhydro-3,5-dideoxy-6-O-(2,2-dimethylpropanoyl)-3,5-dimethyl-4-O-methyl-L-glucitol 
• 467224-41-5 3,5-dideoxy-3,5-dimethyl-4-O-methyl-1,2-O-(1-methylethylidene)-6-C-oxo-β-L-mannoseptanose 
• 183874-37-5 Boc-Val-Thr-OH 
• 191355-74-5 3-deoxy-3-methyl-4-O-methyl-6-O-(4-methylphenylsulfonyl)-1,2-O-(1-methylethylidene)-D-myo-inositol 
• 191355-75-6 1D-(1,2,3,4,5/6)-1,2-anhydro-3,4-O-isopropylidene-5-methyl-6-O-methylcyclohexane-1,2,3,4,6-pentol 
• 191355-76-7 4,6-deoxy-4,6-dimethyl-5-O-methyl-2,3-O-(1-methylethylidene)-D-allo-inositol 

Downstream Products

• 147334-90-5 stevastelin B3 
• 906800-18-8 (3S,6S,9S,12R,13R)-3-Benzyloxymethyl-13-((1S,2R)-2-benzyloxy-1-methyl-pentadecyl)-6-((R)-1-hydroxy-ethyl)-9-isopropyl-12-methyl-1-oxa-4,7,10-triaza-cyclotridecane-2,5,8,11-tetraone 
• 147334-90-5 stevastelin B3 

Relevant articles and documents

Total synthesis of stevastelins: Structure confirmation of stevastelins B and B3, and structure revision of stevastelin C3

The total syntheses of stevastelins B, B3, C3, and the 5-deoxy derivative of stevastelin C3, novel cyclic depsipeptides starting from L-quebrachitol, and amino acids are described. Stereoselective introduction of two methyl groups into L-quebrachitol, followed by regioselective cleavage of the cyclohexane ring by way of the Baeyer-Villiger reaction effectively afforded the fatty acid moiety of stevastelins. Introduction of the peptide and subsequent macrolactamization gave stevastelin B. Stevastelins C3 and B3 were also synthesized by a similar way. The direct comparison of synthetic stevastelins with natural compounds revealed that the synthetic stevastelins B and B3 are identical to the natural products, confirming the proposed structures. However, the synthetic stevastelin C3 was found to not be identical with the natural product. To elucidate the structure of stevastelin C3, degradation of the natural product was carried out to show the possibility that the natural product could be a 5-deoxy derivative of the proposed structure. Thus, the 5-deoxy derivative of the fatty acid moiety was prepared and transformed into a macrocycle. The synthetic 5-deoxy compound was fully identical to natural stevastelin C3. Based on these studies, it was shown that the structure of stevastelin C3 should be revised.

Total synthesis of stevastelins B3 and C3: Structure confirmation of stevastelin B3 and revision of stevastelin C3

The total synthesis of stevastelin B3, stevastelin C3 and 5-deoxy derivative of stevastelin C3, novel 13-membered cyclic depsipeptides, is described. This study unambiguously confirmed the proposed absolute structure of stevastelin B3, and revealed that t