160280-65-9

Basic information

• Product Name: (2R,3R,4R)-1,2,3,4-Octadecanetetrol 2-Methanesulfonate
• Synonyms: (2R,3R,4R)-1,2,3,4-Octadecanetetrol 2-Methanesulfonate;(2R,3R,4R)-
• CAS NO: 160280-65-9
• Molecular Formula: C₁₉H₄₀O₆S
• Molecular Weight: 396.5823
• Product Categories: Aliphatics;Chiral Reagents;Sulfur & Selenium Compounds
• Mol File: 160280-65-9.mol

Chemical Properties

• Boiling Point: 578.217°C at 760 mmHg
• Flash Point: 303.495°C
• Appearance: /
• Density: 1.092g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.491
• Solubility: Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: (2R,3R,4R)-1,2,3,4-Octadecanetetrol 2-Methanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4R)-1,2,3,4-Octadecanetetrol 2-Methanesulfonate(160280-65-9)
• EPA Substance Registry System: (2R,3R,4R)-1,2,3,4-Octadecanetetrol 2-Methanesulfonate(160280-65-9)

Safety Data

• Hazardous Substances Data: 160280-65-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(2R,3R,4R)-1,2,3,4-Octadecanetetrol 2-Methanesulfonate is used as a synthetic building block for the creation of more complex organic molecules. Its unique stereochemistry and functional groups make it a valuable intermediate in the synthesis of various compounds, particularly those with biological or pharmaceutical relevance.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (2R,3R,4R)-1,2,3,4-Octadecanetetrol 2-Methanesulfonate may be utilized as a key component in the development of new drugs. Its specific stereochemistry could be exploited to create molecules with enhanced selectivity and potency, potentially leading to more effective treatments for various diseases.
Used in Chemical Research:
(2R,3R,4R)-1,2,3,4-Octadecanetetrol 2-Methanesulfonate can also be used in academic and industrial research settings to study the effects of stereochemistry on molecular interactions, reactivity, and biological activity. This knowledge can be applied to the design of new molecules with improved properties and applications.
Used in Material Science:
The compound may find applications in material science, where its unique properties could be harnessed to create novel materials with specific characteristics, such as improved stability, reactivity, or selectivity in various chemical processes.

InChI:InChI=1/C19H40O6S/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-17(21)19(22)18(16-20)25-26(2,23)24/h17-22H,3-16H2,1-2H3/t17-,18-,19-/m1/s1

Upstream product

• 849372-21-0 (4R,5R)-1-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-(tert-butyldimethylsilyloxy)ethan-1-one 
• 849372-20-9 (4S,5R)-1-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-(tert-butyldimethylsilyloxy)-1(R)-ethan-1-ol 
• 1431220-30-2 C₃₃H₄₇NO₉S 
• 117168-66-8 1,3-O-benzylidene-2-O-methanesulfonyl-L-xylo-1,2,3,4-octadecanetetrol 
• 117168-65-7 (2R,3R,4S)-1,3-O-benzylidene-1,2,3,4-octadecanetetrol 
• 38084-06-9 6-deoxy-6-iodo-1,2:3,4-di-O-isopropylidene-D-psicofuranose 
• 34626-95-4 1,2:3,4-di-O-isopropylidene-β-D-psicofuranose 
• 1350290-11-7 (2R)-2-(tert-butyldimethylsilyloxy)-1-((4S,5S)-2,2-dimethyl-5-((E)-tetradec-1-enyl)-1,3-dioxolan-4-yl)ethanol 
• 150162-78-0 (2R,3S)-1,3-O-benzylidene-1,2,3-octadecanetriol-4-one 
• 303752-90-1 1,3-O-benzylidene-(D-arabino/L-xylo)-1,2,3,4-octadecanetetrol 
• 117168-55-5 (2R,3R,4R)-1,3-O-benzylidene-1,2,3,4-octadecanetetrol 
• 88303-25-7 tetradecylmagnesium bromide 
• 160280-63-7 Methanesulfonic acid (R)-1-[(4R,5R)-2,2-dimethyl-5-((E)-tetradec-1-enyl)-[1,3]dioxolan-4-yl]-2-trityloxy-ethyl ester 
• 175435-59-3 (R)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-ethane-1,2-diol 

Downstream Products

• 1068608-25-2 2-azido-3,4-O-isopropylidene-1-S-(2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-D-ribo-3,4-octadecanediol 
• 1431220-32-4 C₆₅H₉₅NO₈S 
• 1431220-33-5 C₆₆H₉₇NO₈S 
• 1431220-34-6 C₆₂H₉₁NO₈S 
• 1431220-35-7 C₆₃H₉₃NO₈S 
• 1431220-28-8 C₄₁H₇₃NO₈S 
• 1431220-29-9 C₄₂H₇₅NO₈S 
• 916159-68-7 (2S,3S,4R)-2-azido-1-(tert-butyldiphenylsilyloxy)octadecane-3,4-diol 
• 160280-69-3 (2S,3S,4R)-3,4-di-O-benzyl-N-hexacosanoyl-1-O-trityl-2-amino-3,4-octadecanetriol 
• 160280-67-1 (2S,3S,4R)-2-azido-3,4-di-O-benzyl-1-O-trityl-1,3,4-octadecanetriol 
• 160280-70-6 (2S,3S,4R)-2-hexacosylamino-3,4-di-O-benzyl-1,3,4-octadecanetriol 

Relevant articles and documents

A facile formal synthesis of D-ribo-C18-Phytosphingosine

A facile synthesis of D-ribo-C18-Phytosphingosine from divinylcarbinol via Sharpless asymmetric epoxidation and Sharpless asymmetric dihydroxylation was described.

Synthesis and immunostimulatory activity of two α-S-galactosyl phenyl-capped ceramides

Two α-S-linked galactosylceramides carrying ω-phenyl fatty acid chains were efficiently synthesized and were shown to have in vitro stimulatory activity for human natural killer T cells. ARKAT-USA, Inc.

An efficient synthesis of D-ribo-C18-phytosphingosine and L-arabino-C18-phytosphingosine from D-fructose

D-ribo-C18-phytosphingosine and L-arabino-C18- phytosphingosine were synthesised starting from commercially inexpensive D-fructose. Metal-mediated fragmentation and stereoselective reduction were used as key steps to provide the hydrophilic portion of D-ribo and L-arabino phytosphingosines. Grubbs' cross-metathesis and hydrogenation allowed the incorporation of hydrophobic tail.

Alpha-GLYCOSYL THIOLS AND alpha-S-LINKED GLYCOLIPIDS

The present invention relates to stereoselective methods for the preparation of α-glycosyl thiols and α-S-linked glycosylceramides.

HEPATITIS C VIRUS INHIBITOR COMPRISING ALPHA-GLYCOSYLCERAMIDE AS THE ACTIVE INGREDIENT

This invention provides a growth inhibitor of human hepatitis C virus comprising, as an active ingredient, α-glycosylceramide used for patients infected with the aforementioned viruses. This inhibitor of hepatitis C virus comprises, as an active ingredien

A facile synthesis of phytosphingosine from diisopropylidene-D-mannofuranose

In the present study, an efficient method with a high overall yield for preparing phytosphingosine and an analogue was developed. Starting with commercially available 2,3;5,6-di-O-isopropylidene-D-mannofuranose, a variety of lipid moieties were incorporated to obtain phytosphingosine and an analogue. Through an eight-step manipulation, phytosphingosine was obtained with an overall yield of 57%.

Total synthesis of α-galactosyl cerebroside

A highly convergent synthetic approach was developed to obtain α- galactosyl cerebroside O-(α-D-galactopyranosyl)-2-hexacosylamino-D-ribo- 1,3,4-octadecantriol, which has previously been demonstrated to have immunostimulatory activity. Known 4,6-O-benzyli

Practical Total Synthesis of (2S,3S,4R)-1-O-(α-D-Galactopyranosyl)-N-hexacosanoyl-2-amino-1,3,4- octadecanetriol, the Antitumorial and Immunostimulatory α-Galactosylceramide, KRN7000

A practical total synthesis of (2S,3S,4A)-1-O-(α-D-galactopyranosyl)-N-hexacosanoyl-2-amino-1,3,4- octadecanetriol (KRN7000), an antitumorial and immunostimulatory glycosphingolipid derived from agelasphins, was achieved in 14 steps starting from D-lyxose in a 16% overall yield.

Synthesis of Sphingosines, 11 - Convenient Synthesis of Phytosphingosine and Sphinganine from D-Galactal and D-Arabitol

3,4,6-Tri-O-benzyl-D-galactal (3) was directly converted into 3,4,6-tri-O-benzyl-2-deoxy-D-galactose (5).Wittig reaction of 5 with alkyltriphenylphosphonium salts in the presence of n-butyllithium as the base afforded olefins 6a, b which could be readily transformed into phytosphingosines 1a, b via different routes; (i) at first group introduction and then double bond and protective group removal, and azido group generation via hydrogenation; (ii) 2-O-mesylation, then double bond and benzyl group removal via hydrogenation, and finally nitrogen introduction; (iii) selective double bond hydrogenation, then nitrogen introduction, and finally benzyl group removal and amino group generation via hydrogenation.Wittig reaction of 5 with alkyltriphenylphosphonium salt in the presence of potassium tert-butoxide as the base afforded diene 7a which proved to be a convenient precursor for sphinganine syntheses; thus, 2-O-mesylation, then double bond and benzyl group removal via hydrogenation and 1,3-O-acetylation, and finally nitrogen introduction and de-O-acetylation afforded 23a.Based on the convenient transformation of D-arabitol into the 1,3-O-benzylidene derivative 25 a further phytosphingosine synthesis is outlined. - Key Words: Phytosphingosine / Sphinganine / Galactal / 2-Deoxy-D-galactose / D-Arabitol / Carbohydrates

Sphingosine and Phytosphingosine from D-Threose Synthesis of a 4-Keto-Ceramide

Reaction of 2,4-O-benzylidene-D-threose 3 with tetradecyl magnesium bromide furnished D-arabino- and L-xylo-octadecane-1,2,3,4-tetrols 5a,x.Regioselective oxidation of the 4-OH group gave 4-keto-D-erythro-derivative 6 which can be reduced with acetaldehyde in a SmI2-catalyzed Tishtshenko reaction to afford exclusively 5a.Regioselective 2-O-mesylation of 5a ( -> 7a) and then acid catalyzed debenzylation afforded exclusively 2-O-mesyl-tetrol 9a.Reaction with NaN3 and ensuing azide reduction furnished D-ribo-C18-phytosphingosine (2) in high overall yield.Treatment of 2-O-mesyl derivatives 7a,x with NaN3 and then with 4-nitrobenzenesulfonyl chloride in pyridine afforded 11r,l.Elimination with DBU or, alternatively, by treatment with phenylselenide and then with H2O2, gave known 1,3-O-benzylidene protected azidosphingosine 14, which can be readily converted into sphingosine (1).Transformation of 2 into ceramide 15, selective 1,3-O-silyl protection, oxidation of the 4-OH group ( -> 17) and then desilylation afforded the 4-keto ceramide 18 found in a marine sponge.Reduction of 17 offers a convenient possibility for radioactive labelling of ceramides with tritium.