38838-06-1

Basic information

• Product Name: (3aS,4S,6R,6aR)-4-(iodoMethyl)-6-Methoxy-2,2-diMethyltetrahydrofuro[3,4-d][1,3]dioxole
• Synonyms: (3aS,4S,6R,6aR)-4-(iodoMethyl)-6-Methoxy-2,2-diMethyltetrahydrofuro[3,4-d][1,3]dioxole;(3aS,4S,6R,6aR)-4-(iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole(WXC09221)
• CAS NO: 38838-06-1
• Molecular Formula: C₉H₁₅IO₄
• Molecular Weight: 314.11747
• Mol File: 38838-06-1.mol
• Article Data: 30

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3aS,4S,6R,6aR)-4-(iodoMethyl)-6-Methoxy-2,2-diMethyltetrahydrofuro[3,4-d][1,3]dioxole(CAS DataBase Reference)
• NIST Chemistry Reference: (3aS,4S,6R,6aR)-4-(iodoMethyl)-6-Methoxy-2,2-diMethyltetrahydrofuro[3,4-d][1,3]dioxole(38838-06-1)
• EPA Substance Registry System: (3aS,4S,6R,6aR)-4-(iodoMethyl)-6-Methoxy-2,2-diMethyltetrahydrofuro[3,4-d][1,3]dioxole(38838-06-1)

Safety Data

• Hazardous Substances Data: 38838-06-1(Hazardous Substances Data)

Usage

General Description

The chemical compound (3aS,4S,6R,6aR)-4-(iodoMethyl)-6-Methoxy-2,2-diMethyltetrahydrofuro[3,4-d][1,3]dioxole is a complex organic molecule with a tetrahydrofuran-dioxole ring system. It contains an iodoMethyl group and a methoxy group, as well as two methyl substituents. (3aS,4S,6R,6aR)-4-(iodoMethyl)-6-Methoxy-2,2-diMethyltetrahydrofuro[3,4-d][1,3]dioxole is a potentially useful intermediate for the synthesis of various organic compounds, and its structure suggests that it may have biological activity or pharmaceutical applications. The presence of the iodoMethyl group also makes it a versatile building block for further chemical reactions, making it valuable for use in organic synthesis. Overall, (3aS,4S,6R,6aR)-4-(iodoMethyl)-6-Methoxy-2,2-diMethyltetrahydrofuro[3,4-d][1,3]dioxole is a complex and interesting molecule with potential applications in the fields of organic chemistry and pharmaceutical research.

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 
• 50-69-1 D-ribose 
• 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 
• 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 
• 36468-53-8 β-D-ribofuranose 

Downstream Products

• 301523-39-7 4-benzylamino-1,2,3,4,7,8-hexadeoxy-5,6-O-isopropylidene-D-ribo-oct-1,7-dienitol 
• 1273232-46-4 tert-butyl (3S,4S,5R,αR)-3-[N-but-3'-enyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidenehept-6-enoate 
• 1273232-24-8 tert-butyl (2R,3S,4S,5R,αR)-2-hydroxy-3-[N-but-3'-enyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidenehept-6-enoate 
• 1273232-49-7 tert-butyl (3S,4S,5R,αR)-3-[N-but-3'-enyl-N-(α-methyl-p-methoxybenzyl)amino]-4,5-O-isopropylidenehept-6-enoate 
• 1273232-31-7 tert-butyl (2R,3S,4S,5R,αR)-2-hydroxy-3-[N-but-3'-enyl-N-(α-methyl-p-methoxybenzyl)amino]-4,5-O-isopropylidenehept-6-enoate 
• 158112-55-1 5-O-deoxy-D-ribofuranose 
• 345899-12-9 (1R,2R,3S,4R,5R)-N,2-dibenzyl-3,4-O-isopropylidenedioxy-5-methylpyrrolidine N-oxide 
• 1053711-30-0 N-benzyl-N-[1-(2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-2-phenyl-ethyl]-hydroxylamine 
• 345899-11-8 (1R,2R,3S,4R,5R)-2-allyl-N-benzyl-3,4-O-isopropylidenedioxy-5-methylpyrrolidine N-oxide 
• 1053264-94-0 N-benzyl-N-[1-(2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-3-enyl]-hydroxylamine 

Relevant articles and documents

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.

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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.

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.

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.