13263-74-6

Basic information

• Product Name: 5,5-bis(ethylsulfanyl)pentane-1,2,3,4-tetrol
• Synonyms: 5,5-bis(ethylsulfanyl)pentane-1,2,3,4-tetrol;D-Xylose-diethyldithioacetal;D-Xylose-diethylmercaptal
• CAS NO: 13263-74-6
• Molecular Formula: C₉H₂₀O₄S₂
• Molecular Weight: 256.38
• Mol File: 13263-74-6.mol

Chemical Properties

• Boiling Point: 496.1°Cat760mmHg
• Flash Point: 240.5°C
• Appearance: /
• Density: 1.304g/cm³
• Vapor Pressure: 6.38E-12mmHg at 25°C
• Refractive Index: 1.583
• CAS DataBase Reference: 5,5-bis(ethylsulfanyl)pentane-1,2,3,4-tetrol(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5-bis(ethylsulfanyl)pentane-1,2,3,4-tetrol(13263-74-6)
• EPA Substance Registry System: 5,5-bis(ethylsulfanyl)pentane-1,2,3,4-tetrol(13263-74-6)

Safety Data

• Hazardous Substances Data: 13263-74-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H20O4S2/c1-3-14-9(15-4-2)8(13)7(12)6(11)5-10/h6-13H,3-5H2,1-2H3

Upstream product

• 138661-13-9 2,4:3,5-di-O-benzylidene-D-xylose diethyl dithioacetal 
• 75-08-1 ethanethiol 
• 51885-64-4 1,2-O-isopropylidene-β-L-arabinofuranose 
• 87-72-9 D-Xylose 
• 58-86-6 D-xylose 

Downstream Products

• 138661-13-9 2,4:3,5-di-O-benzylidene-D-xylose diethyl dithioacetal 
• 13039-94-6 2,3,4,5-di-O-isopropylidene-D-xylose aldehyde 
• 103276-78-4 O³,O⁴,O⁵-tribenzoyl-D-xylose diethyl dithioacetal 
• 6893-65-8 5-O-p-toluenesulfonyl-1,2-O-isopropylidene-L-arabinofuranose 
• 87614-55-9 Toluene-4-sulfonic acid (3aR,5S,6R,6aR)-2,2,5-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 37111-48-1 1,2-O-Isopropyliden-5-desoxy-β-L-threo-pentofuranos-3-ulose 
• 101703-63-3 2,3,4,5-tetra-O-benzyl diethyl dithioacetal D-xylose 
• 119278-72-7 D-(1Ξ)-O³,O⁴,O⁵-tribenzoyl-1-methoxy-xylitol 
• 138535-84-9 2,3-di-O-benzyl-D-xylose diethyl dithioacetal 
• 107996-50-9 1,2-O-isopropylidene-3-O-p-toluenesulfonyl-5Z-undecen-1,2R,3R-triol 
• 108713-94-6 (2R,3S,4R)-2,3,4-Tris-benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-pentanal 
• 108713-97-9 methyl (4S,5R,6R)-4,5,6-tris(benzyloxy)-7-hydroxy-2-(methoxycarbonyl)heptanoate 
• 108713-95-7 2-[(2S,3R,4R)-2,3,4-Tris-benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-pentylidene]-malonic acid dimethyl ester 
• 108713-96-8 2-[(2S,3R,4R)-2,3,4-Tris-benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-pentyl]-malonic acid dimethyl ester 

Relevant articles and documents

Photoresist resin monomer and synthesis method thereof

The invention discloses a photoresist resin monomer, which relates to the field of photoresists, and has a structural formula shown in the specification, wherein R1 and R2 are respectively and independently hydrogen, alkane or cycloalkane; R3 is hydrogen or methyl, wherein n is an integer from 1 to 8, and m is an integer from 1 to 10. According to the present invention, the photoresist monomer and other types of resin monomers are subjected to copolymerization to form the photoresist resin, such that the dissolution rate difference of the exposure region and the non-exposure region in the alkaline developing solution can be increased, the roughness can be reduced, the sensitivity and the resolution can be improved, the photoresist pattern with good uniformity can be easily formed, and the method is particularly suitable for the positive photoresist; the etching resistance can also be improved; the starting raw material is naturally extracted saccharide, the raw material source is wide, and the synthesis method is simple.

Regioselective Synthesis of Difluorinated C-Furanosides Involving a Debenzylative Cycloetherification

A highly regioselective synthesis of valuable gem-difluorinated C-furanosides from unprotected aldoses via a debenzylative cycloetherification (DBCE) reaction induced by diethylaminosulfur trifluoride is descibed. The scope and limitations of this DBCE reaction are described using a series of commercially available pentoses and hexoses to afford, without selective protection/deprotection sequences, the corresponding gem-difluorinated C-furanosides in moderate to good yields.

Efficient and regioselective synthesis of γ-lactone glycosides through a novel debenzylative cyclization reaction

An efficient and regioselective approach for the construction of synthetically important γ-lactone glycosides is reported from unprotected aldoses through a new debenzylative lactonization (DBL) reaction. The scope and limitations of this DBL reaction are described starting from a series of commercially available hexoses (l-fucose, d-galactose, d-glucose) and pentoses (d-arabinose, d-ribose, d-lyxose, d-xylose) to afford the corresponding γ-lactones in good yields and without concomitant δ-lactone formation.

Bromodimethylsulfonium bromide (BDMS) mediated dithioacetalization of carbohydrates under solvent-free conditions

A variety of diethyl dithioacetals of sugars can be prepared in very good yields by the reaction of various monosaccharides with ethanethiol in the presence of 3 mol % bromodimethylsulfonium bromide (BDMS) at 0-5 °C. Similarly, dipropyl dithioacetal derivatives can also be obtained in good yields using propanethiol under identical reaction conditions. These dithioacetal derivatives were characterized by per-O-acetylation using silica gel-supported perchloric acid. The significant features of the present protocol are good-to-excellent yields, mild, clean, and solvent-free reaction conditions. This method is extremely suitable for the large-scale preparation of dithioacetal derivatives of various sugars.

Novel D-xylose derivatives stimulate muscle glucose uptake by activating AMP-activated protein kinase α

Type 2 diabetes mellitus has reached epidemic proportions; therefore, the search for novel antihyperglycemic drugs is intense. We have discovered that D-xylose increases the rate of glucose transport in a non-insulin-dependent manner in rat and human myot

Studies on enolization of aldehydo-aldose derivatives

Acetylation of the 2,3-O-isopropylidene derivative (1) of d-glyceraldehyde with hot acetic anhydride in the presence of sodium acetate give a mixture of (Z)- and (E)-enol acetates (2 and 3), together with the acetylated racemic aldehydrol (4) of 1. Likewise, the acyclic aldehydo 2,3:4,5-diisopropylidene acetals of d- and l-arabinose, d-xylose, and d-ribose underwent conversion into enol acetates, with the (Z) isomers preponderating, and convertible photochemically into the corresponding (E) isomers. Under other conditions of acetylation, the aldehydo derivatives were converted into the corresponding aldehydrol diacetates.

Total synthesis of (+)-phorboxazole A, a potent cytostatic agent from the sponge Phorbas sp.

A convergent total synthesis of phorboxazole A (1a), from the C(3-19), C(20-27) and C(33-46) fragments 5, 4 and 91, respectively, concentrating on stereocontrolled formation of the bonds at C(2-3), C(19-20) and C(27-28), is described. Although a coupling reaction between a macrolide ketone and the side chain substituted sulfone, at C(27-28) was not successful, a Wadsworth-Emmons olefination involving the oxane methyl ketone 4 and an oxazole produced the oxane 90 which was next coupled to 91 leading to the C(20-46) unit 100. A further coupling of 100 to 71c at C(19-20) then led to 105, ultimately, and the synthesis was completed by a macrocyclisation reaction from 105, at the C(2-3) alkene bond, followed by deprotection of 106.

Efficient Synthesis of the Hexasaccharide Fragment of Landomycin A: Using Phenyl 2,3-O-Thionocarbonyl-1-thioglycosides as 2-Deoxy-β-glycoside Precursors

(Equation Presented) The β-p-methoxyphenol hexadeoxysaccharide fragment of landomycin A was synthesized in a total of 33 steps and 0.5% overall yield starting from D-mannose and D-xylose, featuring the use of phenyl 2,3-O-thionocarbonyl-1-thioglycosides a

Simple syntheses of 3,4-dideoxy-oct-2-ulosonic acids

Bisacetonated aldehydo-D-arabinose has been converted by three consecutive reactions (Wittig reaction, catalytic hydrogenation, and hydrolysis) into 3,4-dideoxy-D-arabino-oct-2-ulosonic acid (4-deoxy-KDO), isolated as its calcium sal