38838-06-1

Usage

Uses

Used in Organic Synthesis:
(3aS,4S,6R,6aR)-4-(iodoMethyl)-6-Methoxy-2,2-diMethyltetrahydrofuro[3,4-d][1,3]dioxole serves as a versatile intermediate for the synthesis of various organic compounds. Its unique structure and functional groups make it a valuable building block for creating new molecules with specific properties.
Used in Pharmaceutical Research:
Due to its complex structure and the presence of the iodoMethyl group, (3aS,4S,6R,6aR)-4-(iodoMethyl)-6-Methoxy-2,2-diMethyltetrahydrofuro[3,4-d][1,3]dioxole may have biological activity or pharmaceutical applications. It can be further explored and modified to develop potential drug candidates for various therapeutic areas.
Used in Chemical Reactions:
The iodoMethyl group in (3aS,4S,6R,6aR)-4-(iodoMethyl)-6-Methoxy-2,2-diMethyltetrahydrofuro[3,4-d][1,3]dioxole makes it a suitable candidate for various chemical reactions, allowing for the development of new compounds and materials with specific functions and properties.

Upstream product

• 50610-99-6 1-O-methyl-2,3-O-isopropylidene-5-O-(methanesulfonyl)-β-D-ribofuranoside 
• 4137-56-8 methyl 2,3-O-isopropylidene-5-O-p-tolylsulfonyl-β-D-ribofuranoside 
• 77-76-9 2,2-dimethoxy-propane 
• 67-56-1 methanol 
• 532-20-7 D-Ribose 
• 67-64-1 acetone 
• 36468-53-8 β-D-ribofuranose 
• 50-69-1 D-ribose 
• 74925-17-0 2,2,2-Trifluoro-ethanesulfonic acid (3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 
• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 85558-05-0 2-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy)-1,3-diphenyl-[1,3,2]diazaphospholidine 

Downstream Products

• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 155934-55-7 (4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde 
• 158112-55-1 5-O-deoxy-D-ribofuranose 
• 23202-81-5 methyl 5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside 
• 376608-65-0 2-[[(3aR,4S,6R,6aS)-6-aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol (2R,3R)-2,3-dihydroxybutanedioic acid 
• 274693-55-9 [3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol 
• 274693-54-8 benzyl 6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ylcarbamate 
• 866551-95-3 ethyl 2-(6-(benzyloxycarbonylamino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy) acetate 
• 274693-53-7 [3aS-(3aα,4α,6α,6aα)]-(tetrahydro-6-hydroxy-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl)carbamic acid phenylmethyl ester 
• 345898-95-5 N-(((4S,5R)-2,2-dimethyl-5-vinyl-1 ,3-dioxolan-4-yl)methylene)-1-phenylmethanamine oxide 
• 63599-69-9 (3aR,4R,6S,6aR)-4-methoxy-2,2-dimethyl-6-styryltetrahydrofuro[3,4-d][1,3]dioxole 
• 1393792-77-2 tert-butyl (3R,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-dihydroxy-4,5-O-isopropylidene-6-(tert-butyldimethylsilyloxy)hexanoate 
• 1393792-76-1 tert-butyl (3R,4R,5S)-3-(N-benzyl-N-isopropylamino)-4,5-dihydroxy-4,5-O-isopropylidene-6-(tert-butyldimethylsilyloxy)hexanoate 
• 1605346-52-8 tert-butyl (4R,5S,E)-4,5-dihydroxy-4,5-O-isopropylidene-6-benzyloxyhex-2-enoate 

Relevant academic research and scientific papers

Synthesis and Anti-HBV Activity of Thiouracils Linked via S and N-1 to the 5-Position of Methyl β-D-Ribofuranoside

Reverse nucleoside derivatives of 2-(methylsulfanyl)uracils 6a-d were prepared by treating of the sodium salt of 2-(methylsulfanyl)uracils (5a-d) with methyl 2,3-O-isopropylidene-5-O-p-toluenesulfonyl-β-D-ribofuranoside (2). The alkylation of 2-thiouracils 4a-d with methyl 5-deoxy-5-iodo-2,3-O-isopropylidene-D-ribofuranoside (3) afforded the corresponding S-ribofuranoside derivatives 8a-d. Deisopropylidenation of 6a-d and 8a-d afforded the corresponding deprotected derivatives 7a-d and 9a-d, respectively. The Anti-HBV activity of selected compounds was studied.

Alkylcobalamins: formation by enantioselective alkylation of cob(I)alamin, 1H NMR spectra, and conformational analysis of the alkyl group

The 1H NMR spectra of a series of alkylcobalamins, principally 2-oxy substituted, including adenosyl- and ribosylcobalamin, have been analysed with particular attention to the conformation of the alkyl moiety.The enantioselectivity of formation of some of these compounds from their chiral precursors has been determined (NMR analysis) and rationalized.

SYNTHESIS OF HIGHER-CARBON SUGARS BY TRIBUTYLTIN HYDRIDE - AZOBISISOBUTYRONITRILE INDUCED RADICAL ADDITIONS

The Bu3SnH-AIBN induced radical additions of 3,5-di-O-acetyl-6-deoxy-6-iodo-1,2-O-isopropylidene-α-D-gluco- and -allofuranose (1 and 10), and methyl 5-deoxy-5-iodo-2,3-O-isopropylidene-β-D-ribofuranoside (19) to dimethyl maleate, methyl acrylate, acrylonitrile, methyl vinyl ketone, and vinylene carbonate gave various types of higher-carbon sugars.

Structure-property relationships of ribose based ionic liquids

The authors of this work have successfully synthesized a broad choice of new ribose based ionic liquids, using several varying protecting groups (methyl, ethyl, allyl and benzyl) at the various positions of the carbohydrate, as well as different quarternised N-heterocycles and different anions. These consistent variations of the carbohydrate based ionic liquids (CHILs) enabled an extensive structure-property relationship study of thermal properties, allowing the authors to prove existing trends and to find a correlation between the decomposition temperature and the structure of the CHILs.

NOVEL SPIROBICYCLIC ANALOGUES

The present invention relates to novel spirobicyclic analogues of Formula (I) wherein the variables have the meaning defined in the claims. The compounds according to the present invention are useful as PRMT5 inhibitors. The invention further relates to pharmaceutical compositions comprising said compounds as an active ingredient as well as the use of said compounds as a medicament.

Synthesis of Nucleosides through Direct Glycosylation of Nucleobases with 5-O-Monoprotected or 5-Modified Ribose: Improved Protocol, Scope, and Mechanism

Simplifying access to synthetic nucleosides is of interest due to their widespread use as biochemical or anticancer and antiviral agents. Herein, a direct stereoselective method to access an expansive range of both natural and synthetic nucleosides up to a gram scale, through direct glycosylation of nucleobases with 5-O-tritylribose and other C5-modified ribose derivatives, is discussed in detail. The reaction proceeds through nucleophilic epoxide ring opening of an in situ formed 1,2-anhydrosugar (termed “anhydrose”) under modified Mitsunobu reaction conditions. The scope of the reaction in the synthesis of diverse nucleosides and other 1-substituted riboside derivatives is described. In addition, a mechanistic insight into the formation of this key glycosyl donor intermediate is provided.

Method for preparing ticagrelor key intermediate

The invention relates to a chemical synthesis method of ticagrelor key intermediate 2-[[(3aR, 4S, 6R, 6aS)-6-aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxolane-4-yl] oxy]ethanol (a key intermediate A). The method comprises the following steps: taking D-ribose as a raw material, and carrying out ten chemical reaction steps of 1-locus methylation and 2,3-loci isopropylidene protection, 4-locus derivatization, iodination, furan ring-opening, hydroxylamine reaction, palladium on carbon catalytic hydrogenation, amino Cbz protection, hydroxy protection, sodium borohydride reduction ester, Cbz removal protection and the like, thereby obtaining the key intermediate A. The raw materials are cheap and readily available, the preparation process is high in operability, steps of optical resolution, chiral induction and the like are avoided, the total yield is relatively high, and the product quality is better; particularly due to the use of sodium borohydride reduction ester, the preparation cost of ticagrelor is greatly reduced; and the method is suitable for large-scale industrial production.

Highly Substituted Cyclopentane-CMP Conjugates as Potent Sialyltransferase Inhibitors

Sialylconjugates on cell surfaces are involved in many biological events such as cellular recognition, signal transduction, and immune response. It has been reported that aberrant sialylation at the nonreducing end of glycoconjugates and overexpression of sialyltransferases (STs) in cells are correlated with the malignance, invasion, and metastasis of tumors. Therefore, inhibitors of STs would provide valuable leads for the discovery of antitumor drugs. On the basis of the transition state of the enzyme-catalyzed sialylation reaction, we proposed that the cyclopentane skeleton in its two puckered conformations might mimic the planar structure of the donor (CMP-Neu5Ac) in the transition state. A series of cyclopentane-containing compounds were designed and synthesized by coupling different cyclopentane α-hydroxyphosphonates with cytidine phosphoramidite. Their inhibitory activities against recombinant human ST6Gal-I were assayed, and a potent inhibitor 48l with a Ki of 0.028 ± 0.006 μM was identified. The results show that the cyclopentanoid-type compounds could become a new type of sialyltransferase inhibitors as biological probes or drug leads.

Revisiting synthetic preparation of the quorum sensing substrate S-d-ribosyl-l-homocysteine (SRH)

Cleavage of the thioether bond of S-d-ribosyl-l-homocysteine (SRH) by the enzyme S-ribosylhomocysteinase (LuxS) serves as the final biosynthetic step in the generation of the quorum sensing autoinducer AI-2 by bacteria. Herein, a revised chemical synthesis of SRH is presented at convenient scale and purity for in vitro studies of LuxS. Potassium bis(trimethylsilyl)amide (KHMDS) is identified as a judicious base for the formation of the thioether of the target compound from readily-accessible precursors: a thiol nucleophile derived from l-homocystine and a sulfonate-activated d-ribosyl electrophile. The exclusive use of acid-labile protecting groups allows for facile deprotection to the final product, producing the TFA salt of SRH in five synthetic steps and 26% overall yield. The chemically-synthesized material is isolated at high purity and demonstrated to serve as the LuxS substrate by an in vitro assay.

A carbohydrate-based julia-kocienski reagent for syntheses of chain-extended and C-linked saccharides

The carbohydrate-derived Julia-Kocienski reagent 2-{[(3aS,4S,6R,6aR)-6- methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methylsulfonyl}-1, 3-benzothiazole (6) was prepared from d-ribose and investigated in the eponymous olefination. The base-promoted generation of the Julia anion induced a rearrangement to the corresponding l-lyxose epimer 2-{[(3aS,4R,6R,6aR)-6- methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methylsulfonyl}-1, 3-benzothiazole (12), which reacted readily with aldehydes and with a gluconolactone. The latter reaction furnished an exo-glycal-linked C-diglycoside. Georg Thieme Verlag Stuttgart, New York.