General method for preparation of sphingosine bases and their an

Details General method for preparation of sphingosine bases and their an General method for preparation of sphingosine bases and their an

1994-06-27

1995-06-20

Raymond, Richard L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

564487, 564507, C07C20968, C07C20962

Patent

active

054262283

ABSTRACT:
Described herein is a novel method of preparing selectively diastereomers of sphingosine bases and their analogues of general formula (1a) or (1b) ##STR1## where R is an aliphatic or aromatic substituent containing a straight, branched or cyclic chain, which may include one or several heteroatoms as chain members and one or several functional groups as substituents. The method comprises the steps of:

REFERENCES:
patent: 5012000 (1991-04-01), Illig et al.
Synthetic Studies Toward Amino Alcohols. Diasterocontrolled Reduction of .alpha.'-Chiral, .alpha.,.beta.-Enones. Tetrahedron Letters, vol. 34, No. 42, pp. 6765-6768, 1993.
Horner-Wittig Reaction of Dimethyl 2, 3-O-isopropylidene-D-glyceroylmethylphosphonate and its Application to the formla Synthesis of D-erythro-C.sub.18 -Sphingosine, Yamamoi et al., Chemistry Letters, pp. 335-336, 1989.
A Stereodivergent Synthesis of D-erytho-Sphingosine and D-threo-Sphingosine from L-Serine, Garner et al., J. Org. Chem. 1988, 53, pp. 4395-4398.
Synthesis of D-erythro- and D-threo-Sphingosine Derivatives from L-Serine, Herold, Helv. Chim. Acta 71, pp. 354-362, 1988.
A Stereoselective Synthesis of Sphingosine, A Protein Kinase C Inhibitor, Nimkar et al., Tetrahedron Letters, vol. 29, No. 25, pp. 3037-3040, 1988.
.alpha.-Amino Acid Derivatives as Chiral Educts for Asymmetric Products Synthesis of Sphingosine from .alpha.'-Amino-.alpha.,.beta.-ynones, Boutin et al., J. Org. Chem. 1986, 51, pp. 5320-5327.
.tau.-Amino-.beta.-keto Phosphonates in Synthesis: Synthesis of the Sphingosine Skeleton, Koskinen et al., Synlett, Nov. 1990, pp. 665-666.

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