1253800-18-8

Basic information

• Product Name: (3aR,5S,6R,6aR)-6-benzyloxy-2,2-dimethyl-5-vinyl-5-[(1S)-1-hydroxybut-3-enyl]tetrahydrofuro[2,3-d][1,3]dioxole
• Synonyms: (3aR,5S,6R,6aR)-6-benzyloxy-2,2-dimethyl-5-vinyl-5-[(1S)-1-hydroxybut-3-enyl]tetrahydrofuro[2,3-d][1,3]dioxole
• CAS NO: 1253800-18-8
• Molecular Weight: 346.423
• Mol File: 1253800-18-8.mol

Chemical Properties

• CAS DataBase Reference: (3aR,5S,6R,6aR)-6-benzyloxy-2,2-dimethyl-5-vinyl-5-[(1S)-1-hydroxybut-3-enyl]tetrahydrofuro[2,3-d][1,3]dioxole(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,5S,6R,6aR)-6-benzyloxy-2,2-dimethyl-5-vinyl-5-[(1S)-1-hydroxybut-3-enyl]tetrahydrofuro[2,3-d][1,3]dioxole(1253800-18-8)
• EPA Substance Registry System: (3aR,5S,6R,6aR)-6-benzyloxy-2,2-dimethyl-5-vinyl-5-[(1S)-1-hydroxybut-3-enyl]tetrahydrofuro[2,3-d][1,3]dioxole(1253800-18-8)

Safety Data

• Hazardous Substances Data: 1253800-18-8(Hazardous Substances Data)

Upstream product

• 106-95-6 allyl bromide 

Downstream Products

• 1253800-22-4 (3aR,5R,6R,6aR)-5-[(1S)-1-acetoxybut-3-enyl]-6-benzyloxy-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole 
• 1253800-20-2 (3aR,5R,6R,6aR)-6-benzyloxy-2,2-dimethyl-5-vinyl-5-[(1S)-1-benzyloxybut-3-enyl]tetrahydrofuro[2,3-d][1,3]dioxole 

Relevant articles and documents

Synthesis of a carbohydrate-derived 1-oxaspiro[4.4]nonane skeleton and its conversion into spironucleosides

An easy entry to the 1-oxaspiro[4.4]nonane skeleton has been developed starting from a d-glucose-derived substrate. The key steps involve (a) installation of olefin moieties at the appropriate places through simple transformations and (b) construction of spiro rings by utilizing ring-closing metathesis reactions between these olefin functionalities. Subsequent deprotection of the acetonide functionality, peracetylation, nucleosidaton under Vorbrggen reaction conditions, and final deprotections result in the formation of the spironucleosides. The involvement of an interesting intra/intermolecular acetyl migration has been used to rationalize the product distribution during desilylation. Various 1D and 2D NMR techniques and X-ray analyses of some important intermediates were used for assigning the structures and stereochemistry of the products. Georg Thieme Verlag Stuttgart New York.