17087-84-2

Usage

Molecular weight

447.25 g/mol

Appearance

White solid

Solubility

Soluble in organic solvents such as pyridine, DMSO, and DMF

Functional groups

Isopropylidene group, furanosyl ring, and chloride group

Derivative of α-D-mannose

A sugar molecule commonly found in nature

Use in organic synthesis

Protects hydroxyl groups

Building block in carbohydrate chemistry

Used in the synthesis of complex carbohydrate derivatives and glycoconjugates

Selective manipulation

The isopropylidene group allows for selective manipulation of other parts of the molecule

Versatile chemical reagent

Used in the production of various complex carbohydrate compounds.

Upstream product

• 7757-38-2 O²,O³,O⁵,O⁶-diisopropylidene D-mannofuranose 
• 7757-38-2 2,3,5,6-di-O-isopropylidene-D-mannofuranose 
• 141561-24-2 (2,3:5,6-Di-O-isopropyliden-β-D-mannofuranosyl)-methyl-disulfid 
• 62-53-3 aniline 
• 882-33-7 diphenyldisulfane 
• 14131-84-1 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 
• 357604-61-6 2,3:4,6-di-O-isopropylidene-D-mannopyranose 
• 7757-38-2 (3aS,6R,6aS)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol 
• 3458-28-4 D-Mannose 
• 530-26-7 D-Mannose 
• 7757-38-2 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 

Downstream Products

• 250369-66-5 [4-benzyloxy-2-ethoxy-5-(1-hydroxy-ethyl)-tetrahydro-furan-3-yl]-acetic acid ethyl ester 
• 250369-67-6 (5-acetyl-4-benzyloxy-2-ethoxy-tetrahydro-furan-3-yl)-acetic acid ethyl ester 
• 250369-64-3 C₁₉H₂₈O₇ 
• 79241-07-9 (R)-4-((2S,3R)-3-(benzyloxy)-2,3-dihydrofuran-2-yl)-2,2-dimethyl-1,3-dioxolan 
• 250369-59-6 (3aR,4R,5S,6aR)-5-Acetyl-4-benzyloxy-tetrahydro-furo[2,3-b]furan-2-one 
• 1186034-75-2 1,4-anhydro-5,6-O-isopropylidene-2-deoxy-1-C-phenyl-D-arabino-hex-1-enitol 
• 505081-54-9 (2R,3R,7S,7aS)-3-hydroxy-7-methyl-2-((E)-prop-1-en-1-yl)-2,3,7,7a-tetrahydro-5H-furo[3,4-b]pyran-5-one 

Relevant academic research and scientific papers

Highly regioselective and stereoselective synthesis of C-Aryl glycosidesvianickel-catalyzedortho-C-H glycosylation of 8-aminoquinoline benzamides

C-Aryl glycosides are of high value as drug candidates. Here a novel and cost-effective nickel catalyzedortho-CAr-H glycosylation reaction with high regioselectivity and excellent α-selectivity is described. This method shows great functional group compatibility with various glycosides, showing its synthetic potential. Mechanistic studies indicate that C-H activation could be the rate-determining step.

Straightforward synthesis of protected 2-hydroxyglycals by chlorination-dehydrochlorination of carbohydrate hemiacetals

A straightforward and scalable method for the synthesis of protected 2-hydroxyglycals is described. The approach is based on the chlorination of carbohydrate-derived hemiacetals, followed by an elimination reaction to establish the glycal moiety. 1,2-dehy

Synthesis of Bioactive Side-Chain Analogues of TAN-2483B

The fungal metabolite TAN-2483B has a 2,6-trans-relationship across the pyran ring of its furo[3,4-b]pyran-5-one core, which has thwarted previous attempts at its synthesis. We have now developed a chiral pool approach to this core and prepared side-chain

Efficient Synthesis of α-Glycosyl Chlorides Using 2-Chloro-1,3-dimethylimidazolinium Chloride: A Convenient Protocol for Quick One-Pot Glycosylation

A mild and convenient method for the synthesis of α-glycosyl chlorides in high 80–96 % yields within 15–30 min using 2-chloro-1,3-dimethylimidazolinium chloride (DMC) is disclosed. The method has a wide substrate scope and is compatible with labile OH protecting groups, including benzyl, acetyl, benzoyl, isopropylidene, benzylidene, TBDMS (tert-butyldimethylsilyl), and TBDPS (tert-butyldiphenylsilyl) groups. The excellent α selectivity obtained in this reaction is attributed to in-situ isomerization of β-glycosyl chlorides to the more stable α-glycosyl chlorides, as demonstrated by 1H NMR spectroscopic studies. Disarmed sugars with OBz or OAc groups at C-2 were chlorinated at a faster rate but ismomerized (β→α) at a slower rate than armed sugars with an OBn group at C-2. More importantly, the method enables highly desirable one-pot glycosylation reactions to take place, thus allowing efficient syntheses of disaccharides and simple O-glycosylated sugars in high overall yields without the need for separation or purification of the α-glycosyl chloride donors. This method will be especially useful for direct glycosylation reactions using glycosyl chloride donors that are unstable upon separation and purification.

Synthesis of triazolylmethyl-linked nucleoside analogs via combination of azidofuranoses with propargylated nucleobases and study on their cytotoxicity

[Figure not available: see fulltext.] Copper(I)-catalyzed azide–alkyne 1,3-dipolar cycloaddition reactions (CuAAC) between azidofuranoses and propargyl-nucleobases were carried out in the presence of CuSO4·5H2O and sodium ascorbate as catalytic system to provide the corresponding 1,4-disubstituted-1,2,3-triazole-bridged nucleoside analogs in good yields. Twelve new sugar-based triazolylmethyl-linked nucleoside analogs were synthesized and screened for their cytotoxic activity against MDA-MB-231, Hep3B, PC-3, SH-SY5Y, and HCT-116 cancer cell lines and control cell line (L929). Most of the compounds were moderately effective against all the cancer cell lines assayed. Particularly, among the tested compounds, 1,2,3-triazole-linked 5-fluorouracil–mannofuranose hybrid was found to be the most potent cytotoxic agent against HCT-116, Hep3B, SH-SY5Y cells with IC50 values of 35.6, 71.1, and 75.6 μM, respectively. None of the triazolylmethyl-linked nucleoside analogs exhibited cytotoxic effect against the control cells L929.

Solvent-free synthesis of glycosyl chlorides based on the triphenyl phosphine/hexachloroacetone system

Glycosyl chlorides, useful as glycosyl donors in glycoside synthesis and precursors in organic synthesis, can be easily prepared under solvent-free conditions by exposing a sugar hemiacetal to an equimolar mixture of PPh3 and hexachloroacetone

Synthesis of furanoid and pyranoid C-1 aryl glycals by reaction of glycosyl chlorides with organolithium reagents

Furanosyl and pyranosyl chlorides react with aryllithium derivatives, obtained by directed ortho-lithiation of activated arenes, to give C-1 aryl glycals in moderate yields.

Synthesis of C-1 alkyl and aryl glycals from pyranosyl or furanosyl chlorides by treatment with organolithium reagents

Glycosyl chlorides, with ether or isopropylidene acetal protecting groups, readily available from furanoses or pyranoses, can be conveniently transformed into C-1 alkyl or aryl glycals by reaction with alkyl or aryl organolithium reagents.

A mild and general method for preparation of α-glycosyl chlorides

A mild and efficient chlorination method for production of glycosyl chlorides is first described which employs inexpensive trichlorotriazine (TCT) and DMF as a chlorination reagent and is compatible with typical acid-labile hydroxyl protecting functions. The scope and limitations, reaction mechanism and its application in the sequential glycosylations are discussed.

An approach to an enantioselective synthesis of crisamicin A via a novel double Hauser-Kraus annulation strategy

A double Hauser-Kraus annulation between biscyanophthalide 4 and the d-mannose derived enone 39 provides access to an advanced intermediate 54 that is an excellent scaffold to effect an enantioselective total synthesis of crisamicin A 1.