132729-37-4

Basic information

• Product Name: Trehalostatin
• Synonyms: Trehalostatin;trehazolin;(3aR)-4,5,6,6aα-Tetrahydro-4α,5β,6α-trihydroxy-2-(α-D-glucopyranosylamino)-3aαH-cyclopentoxazole-4β-methanol;A-70615
• CAS NO: 132729-37-4
• Molecular Formula: C13H22N2O10
• Molecular Weight: 366.32118
• Mol File: 132729-37-4.mol

Chemical Properties

• Boiling Point: 767.8°Cat760mmHg
• Flash Point: 418.1°C
• Appearance: /
• Density: 2.25g/cm³
• Vapor Pressure: 3.23E-27mmHg at 25°C
• Refractive Index: 1.825
• CAS DataBase Reference: Trehalostatin(CAS DataBase Reference)
• NIST Chemistry Reference: Trehalostatin(132729-37-4)
• EPA Substance Registry System: Trehalostatin(132729-37-4)

Safety Data

• Hazardous Substances Data: 132729-37-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H22N2O10/c16-1-3-4(18)5(19)6(20)11(24-3)15-12-14-9-8(25-12)7(21)10(22)13(9,23)2-17/h3-11,16-23H,1-2H2,(H,14,15)/t3-,4-,5+,6-,7-,8-,9-,10+,11+,13+/m1/s1

Upstream product

• 172909-56-7 (3aR,4R,5S,6S,6aS)-4-Hydroxymethyl-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-ylamino)-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazole-4,5,6-triol 
• 144811-37-0 1-<<<3aR-(3aα,4α,5β,6α,6aα)>-5-(Benzyloxy)-4-<(benzyloxy)methyl>-3a,5,6,6a-tetrahydro-4,6-dihydroxy-4H-cyclopentoxazol-2-yl>amino>-1-deoxy-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose 
• 138416-78-1 octa-N,O-acetyltrehazolin 
• 147237-45-4 1-Deoxy-1-<<<3aR-(3aα,4α,5β,6α,6aα)>-4-(hydroxymethyl)-3a,5,6,6a-tetrahydro-4,5,6-trihydroxy-4H-cyclopentoxazol-2-yl>amino>-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose 
• 151061-97-1 trehazolamine 
• 147237-44-3 N'-(2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl)-N-<<1R-(1α,2β,3α,4β,5β)>-1-(hydroxymethyl)-1,2,3,4-tetrahydroxycyclopent-5-yl>thiourea 
• 93173-26-3 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl isothiocyanate 
• 147237-45-4 2,3,4,6,-tetra-O-benzyltrehazolin 
• 154540-30-4 <1R-(1α,2β,3α,4β,5β)>-5-Acetamido-1,3,4-triacetoxy-1-(acetoxymethyl)-2-(benzyloxy)cyclopentane 
• 149091-75-8 <1R-(1α,2β,3α,4β,5β)>-5-Acetamido-1,2,3,4-tetraacetoxy-1-(acetoxymethyl)cyclopentane 
• 149091-76-9 <1R-(1α,2β,3α,4β,5β)>-5-Azido-2-(benzyloxy)-1-(hydroxymethyl)-3,4-bis(methoxymethoxy)-1-cyclopentanol 
• 149091-77-0 <1R-(1α,2β,3α,4β,5β)>-5-Acetamido-2-(benzyloxy)-1-(hydroxymethyl)-3,4-bis(methoxymethoxy)-1-cyclopentanol 
• 160799-84-8 (1R,2R,3S,4R,5S)-2-Amino-5-benzyloxy-1-hydroxymethyl-3,4-bis-methoxymethoxy-cyclopentanol 
• 144811-36-9 N-(2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl)-N'-<<1R-(1α,2β,3α,4β,5β)>-2-(benzyloxy)-1-<(benzyloxy)methyl>-1,3,4-trihydroxycyclopent-5-yl>thiourea 

Related news

Stereoselective synthesis of aminocyclitol moieties of trehazolin and Trehalostatin (cas 132729-37-4) via enyne metathesis protocol08/24/2019

Stereoselective and efficient synthesis of respective aminocyclitol moieties 1a and 2a of trehazolin and trehalostatin as hexaacetates 1b and 2b using ring-closing enyne metathesis as the key reaction is described.detailed

Relevant articles and documents

Biosynthesis of the trehalase inhibitor trehazolin

Trehazolin (1) is a trehalase inhibitor produced by Micromonospora coriacea. Biosynthesis of 1 was studied by feeding experiments with a variety of labeled precursors. Feeding experiments with [1-13C]- and [6-13C]-D-glucose revealed that the carbon skeletons of both a glucose residue and a cyclopentane ring moiety in 1 were each derived from glucose, and that C-C bond formation between C-1 and C-5 of glucose occurred during the cyclopentane ring formation. Furthermore, an experiment with [guanidino-13C, 15N2]-L-arginine revealed that two nitrogen atoms and a quaternary carbon atom involved in the aminooxazoline moiety of 1 originated from an amidino group of arginine. Further feeding experiments with [1-2H]-, [2-2H]-, [4-2H]-, [6,6-2H2]- and [1,2,3,4,5,6,6-2H7]-D-glucose as well as [1-13C]-D-fructose showed that deuteriums on C-1, C-3, C-4 and C-6 of glucose were retained during the formation of the cyclopentane ring moiety of 1.

Synthesis of trehazolin from D-glucose

Trehazolin (2) is a specific inhibitor of trehalase, an enzyme that cleaves the reserve carbohydrates of many insects. We describe a short and efficient synthesis of trehazolin (2) and trehazolamine (5) that mimics its hypothetical biosynthesis. Starting molecule for the synthesis of trehazolamine (5) is glucose from which three chiral centers are conserved during the reaction sequence. The remaining two chiral centers of trehazolamine (5) are formed stereoselectively in a reductive cyclization of ketooxime ether 16 and the reduction of oxime ether 18. The overall yield of trehazolamine (5) is 22% over 8 steps from 15. The synthesis of trehazolin (2) from trehazolamine (5) follows a known procedure and is achieved in 63% over 3 steps.

Total Synthesis of the Trehalase Inhibitors Trehalostatin and Trehazolin, and of Their Diastereoisomers. Final Structural Confirmation of the Inhibitor

Potent trehalase inhibitors 1-4 have been synthesized, thereby establishing both the structure and the absolute configuration of the known inhibitor trehazolin 2.Compound 1, previously proposed as the structure of trehalostatin, and its diastereoisomer 3,

Syntheses of trehazolin, trehalamine, and the aminocyclitol moiety of trehazolin: Determination of absolute configuration of trehazolin

The syntheses and determination of the absolute configuration of trehazolin (1), its aglycon (trehalamine (3), and its aminocyclitol hexaacetate moiety (5) are described. An important intermediate, optically active epoxide 16α, was obtained from an 11-ste

Total Synthesis of Trehalase Inhibitor, Trehazolin

The total synthesis of trehalase inhibitor, trehazolin has been accomplished by coupling the optically active aminocyclopentanepentaol with α-D-glucopyranosylisothiocyanate derivative, followed by subsequent oxazoline-ring formation and removal of the pro