153186-11-9

Basic information

• Product Name: {(1S,3S,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]-bicyclo[3.3.0]oct-3-yl}methan-1-ol
• Synonyms: {(1S,3S,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]-bicyclo[3.3.0]oct-3-yl}methan-1-ol
• CAS NO: 153186-11-9
• Molecular Weight: 400.472
• Mol File: 153186-11-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: {(1S,3S,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]-bicyclo[3.3.0]oct-3-yl}methan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: {(1S,3S,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]-bicyclo[3.3.0]oct-3-yl}methan-1-ol(153186-11-9)
• EPA Substance Registry System: {(1S,3S,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]-bicyclo[3.3.0]oct-3-yl}methan-1-ol(153186-11-9)

Safety Data

• Hazardous Substances Data: 153186-11-9(Hazardous Substances Data)

Upstream product

• 100-44-7 benzyl chloride 
• 63593-03-3 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose 
• 100-39-0 benzyl bromide 
• 473290-44-7 1-({(1S,3R,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]-bicyclo[3.3.0]oct-3-yl}methoxy)-2,2-dimethyl-1,1-diphenyl-1-silapropane 
• 63593-02-2 3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose 
• 57099-04-4 3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 
• 22331-21-1 1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose 
• 212970-72-4 {3-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-(1S,3R,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)bicyclo[3.3.0]oct-3-yl}methan-1-ol 

Downstream Products

• 473290-47-0 (3aR,5S,6S,6aR)-6-Benzyloxy-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde 
• 473290-51-6 (E)-3-((2S,3R,5R)-3-Benzyloxy-2-benzyloxymethyl-5-methoxy-4-oxo-tetrahydro-furan-2-yl)-acrylic acid methyl ester 
• 473290-50-5 (E)-3-((2S,3S,4R,5R)-3-Benzyloxy-2-benzyloxymethyl-4-hydroxy-5-methoxy-tetrahydro-furan-2-yl)-acrylic acid methyl ester 
• 473290-49-2 methyl (2E)-3-{(1S,3R,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]-bicyclo[3.3.0]oct-3-yl}prop-2-enoate 
• 473290-53-8 (E)-3-[(2S,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-methoxy-4-tetradec-(Z)-ylidene-tetrahydro-furan-2-yl]-acrylic acid methyl ester 
• 473290-57-2 methyl (2E)-3-{(2S,3S)-5-oxo-3-(phenylmethoxy)-2-[(phenylmethoxy)methyl]-4(E)-tetradecylidene[2-(2,3-dihydrofuryl)]}prop-2-enoate 
• 473290-55-0 methyl (2E)-3-{(2S,3S)-5-oxo-3-(phenylmethoxy)-2-[(phenylmethoxy)methyl]-4(Z)-tetradecylidene[2-(2,3-dihydrofuryl)]}prop-2-enoate 

Relevant articles and documents

Conformationally constrained analogues of diacylglycerol (DAG). Part 19: Asymmetric syntheses of (3R)- and (3S)-3-hydroxy-4,4-disubstituted heptono-1,4-lactones as protein kinase C (PK-C) ligands with increased hydrophilicity

The stereospecific introduction of (R)- and (S)-OH groups at position C-3 of two diacylglycerol γ-lactones (DAG-lactones) previously identified as strong protein kinase C (PK-C) ligands is presented. The compounds were designed to investigate whether the extra OH group in a specific orientation could establish an additional hydrogen bond with the C1 domain of PK-C, thus providing a DAG analogue with reduced lipophilicity. The OH groups were introduced following two different diastereoselective multistep syntheses starting from diacetone-D-glucose. The PK-C binding affinities for the new compounds were weaker in comparison to those of the parent compounds, suggesting that the extra OH does not engage efficiently in hydrogen bonding at the receptor.

Synthesis of 4'-C-methylnucleosides.

Several 4'-C-methylnucleosides were prepared. 1H-NMR studies on these nucleotides showed that they have the 3'-exo furanose ring conformation different from the 3'-endo conformation of natural nucleosides.