380893-75-4

Upstream product

• 42969-65-3 (R)-(+)-3-butyn-2-ol 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 1413383-02-4 (2S,3S,5R,6S,1′R)-3-benzyloxy-2-benzyloxymethyl-6-(1′-tert-butyldiphenylsilyloxyethyl)-1-azabicyclo[3.2.0]heptan-7-one 
• 1413383-00-2 (2S,3S,5R,6R)-3-(benzyloxy)-2-(benzyloxymethyl)-6-((R)-1'-(tert-butyldiphenylsilyloxy)ethyl)-1-azabicyclo[3.2.0]heptan-7-one 
• 1413383-23-9 (2S,3S,4S,5S,6S)-3,4-di(benzyloxy)-2-(benzyloxymethyl)-6-((R)-1'-(tertbutyldiphenylsilyloxy)ethyl)-1-azabicyclo[3.2.0]heptan-7-one 
• 1413383-21-7 (2S,3S,4S,5S,6R)-3,4-di(benzyloxy)-2-(benzyloxymethyl)-6-((R)-1'-(tertbutyldiphenylsilyloxy)ethyl)-1-azabicyclo[3.2.0]heptan-7-one 
• 1413383-10-4 C₄₆H₅₁NO₅Si 
• 1413383-17-1 (2S,3S,4S,5S,Z)-3,4-di(benzyloxy)-2-(benzyloxymethyl)-6-ethylidene-1-azabicyclo[3.2.0]heptan-7-one 
• 1300116-89-5 N-benzyl-N-[(3R)-3-(tert-butyldiphenylsilyloxy)but-1-ynyl]-4-methylbenzenesulfonamide 
• 1300116-84-0 (3R)-1-bromo-3-[(tert-butyldiphenylsilyl)oxy]but-1-yne 
• 863604-43-7 (12R,16R)-2,2-dimethylpropionic acid 16-(tert-butyldiphenylsilanyloxy)-12-hydroxyheptadec-14-ynyl ester 

Relevant academic research and scientific papers

Desymmetrisation of meso propargylic diols

Meso acetylenic diols, conveniently separated from their threo isomers via the corresponding adducts with bromine, have been converted into optically pure derivatives by either lipase-catalysed hydrolysis of the corresponding diacetates or ketalisation of (+)-menthone.

Derivatives of hexahydrobenzofuranone useful for the treatment of (inter alia) auto-immune or inflammatory disorders

Heterocyclic-substituted compounds of formula (I) or a pharmaceutically acceptable salt thereof, are disclosed, wherein: Z is - (CH2)n-; (a); (b), wherein R 10 is absent; or, (c) wherein R 3 is absent; the single dotted line represents an optional double bond; the double dotted line represents an optional single bond; n is 0-2; Het is an optionally substituted mono-, bi- or tri-cyclic heteroaromatic group; B is -(CH 2 ) n3 -. wherein n 3 is 0-5, -CH 2 -O-, -CH 2 S-, -CH 2 -NR 6 -, -C(O)NR 6 -. -NR 6 C(O)-, (d), optionally substituted alkenyl or optionally substituted alkynyl; X is -O- or -NR 6 - when the double dotted line represents a single bond, or X is H, -OH or -NHR 20 when the bond is absent; Y is =O, =S, (H, H), (H, OH) or (H, C 1 -C 6 alkoxy) when the double dotted line represents a single bond or when the bond is absent, Y is =O, =NOR 17 (H, H). (H, OH), (H, SH), (H, C 1 -C 6 alkoxy) or (H, substituted-amino); R 22 and R 23 are independently -OH, -OC(O)R 30 , OC(O)NR 30 R 31 , or optionally substituted alkyl, alkenyl, alkynyl, heterocycloalkyl, aryl, cycloalkyl, cycloalkenyl, carbonyl, amino, alkoxy, alkenyloxy, alkynyloxy, heterocycloalkyloxy, cycloalkyloxy, or cycloalkenyloxy; or R 22 and R 10 , or R 23 and R 11 , can form a carbocyclic or heterocyclic ring; and the remaining variables are as described in the specification, Also disclosed are pharmaceutical compositions containing said compounds and their use as thrombin receptor antagonists and blinders to cannabinoid receptors.

Formation of chiral C(sp3)-C(sp) bond by allylic substitution of secondary allylic picolinates and alkynyl copper reagents

(Chemical Equation Presented) To establish allylic substitution of secondary allylic alcohol derivatives with alkynyl copper reagents, allylic esters bearing the (2-pyridine)CO2-, (2-pyrazine)CO2-, (EtO)2PO2-, C6F5CO2-, o-(Ph2P)-C6H4CO2-, MeOCO 2-, or. AcO- group were examined. First, picolinate (R 1=Me, R2=CH2OPMB) was subjected to reaction with (TMS-C≡C)2CuLi 3 LiBr at 0 °C. Although no substitution took place, MgBr2 (3 equiv) was found to promote the reaction to produce the anti SN2′ product in 93% yield with 94% regioselectivity and 99% chirality transfer. In contrast, substitution of the other esters with the copper reagent in the presence of MgBr2 were less reactive ((2-pyrazine)CO2-) or marginally reactive (other cases). Generality of the substitution using picolinates was established with five picolinates (R1=Me, Ph(CH2)2, PMBO(CH 2)3; R2=Me, CH2OPMB, CH 2OTBS, C5H11, c-C6H11) and seven alkynyl copper reagents (R3=TMS, Ph, p-TBSOC 6H4, p- and o-MeOC6H4, p-MeC 6H4, p-FC6H4), furnishing anti SN2′ products in 61-93% yields with high regioselectivity (usually >90%) and high chirality transfer (usually >95%). In addition, transformation of the products was briefly studied. 2009 American Chemical Society.