http://rdf.ncbi.nlm.nih.gov/pubchem/patent/DE-4240219-A1

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filingDate 1992-11-30-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_adff2c2b870df4b289681f199d10e634
http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_f7d87248b2aee9d16f6a968cb1278787
publicationDate 1994-06-01-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber DE-4240219-A1
titleOfInvention Process and intermediates for the production of ceramide 3 and related compounds
abstract Prepn. of 2-O-sulphonyl or 2-O-sulphato-tetrol derivs. of formula (I) comprises: (a) reacting a 1,3-O-protected tetrol of formula (IIa) with a sulphonylating or sulphating agent and then removing the 1,3-O-protecting gp. from the resulting 2-O-sulphonate or 2-O-sulphate of formula (IV); or (b) hydrogenating the double bond in a 2-O-sulphonyl or 2-O-sulphatotetrol-6-ene of formula (XV); or (c) activating the free 2-O-hydroxyl gp. of a tetrol of formula XVIII by reaction with a sulphonylating or sulphating agent. The protecting gp. R3 is then opt. removed or opt. introduced, as necessary. R1 = 5-19C alkyl opt. contg. OH gps. Me side chains and double bonds; R2 = lower aliphatic or monocyclic opt. substd. aromatic sulphonic acid or sulphate; R3 = H or hydroxy protecting gp.; R4, R5 = H, lower alkyl or opt. substd. aryl. USE/ADVANTAGE - (I) and the other cpds. are intermediates in the prepn. of ceramide 3 and related cpds. which are key components in building barrier layers in the stratum corneum in plants and animals and can be used e.g. in skin-care and hair-care products. The process is diastereospecific, and gives (I) in D-arabino config. starting ultimately from D-arabinose, D-galactose or D-xylose, using relatively few steps.
priorityDate 1992-11-30-04:00^^<http://www.w3.org/2001/XMLSchema#date>
type http://data.epo.org/linked-data/def/patent/Publication

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