147705-04-2

Basic information

• Product Name: decarestrictine N
• Synonyms: decarestrictine N
• CAS NO: 147705-04-2
• Molecular Formula: C10H16 O5
• Molecular Weight: 216.23
• Mol File: 147705-04-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 442.7°Cat760mmHg
• Flash Point: 176.2°C
• Appearance: /
• Density: 1.278g/cm³
• Vapor Pressure: 1.07E-09mmHg at 25°C
• Refractive Index: 1.53
• CAS DataBase Reference: decarestrictine N(CAS DataBase Reference)
• NIST Chemistry Reference: decarestrictine N(147705-04-2)
• EPA Substance Registry System: decarestrictine N(147705-04-2)

Safety Data

• Hazardous Substances Data: 147705-04-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H16O5/c1-6-4-7(11)2-3-8(12)9(13)5-10(14)15-6/h2-3,6-9,11-13H,4-5H2,1H3/b3-2-/t6-,7-,8-,9-/m1/s1

Upstream product

• 1030835-90-5 (E)-4,5-bis(benzyloxy)-8-[(2-methoxyethoxy)methoxy]-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-one 
• 1566591-44-3 (3aS,7S,9S,11aS,E)-9-(methoxymethoxy)-2,2,7-trimethyl-3a,4,8,9-tetrahydro-7H-[1,3]dioxolo[4,5-d]oxecin-5(11aH)-one 
• 1566591-43-2 (2S,4S)-4-(methoxymethoxy)hex-5-en-2-yl 2-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)acetate 
• 1566591-35-2 2-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)acetic acid 
• 1566591-36-3 C₉H₁₄O₃ 
• 658713-40-7 2-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-ethanol 
• 1566591-33-0 tert-butyl-(2-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)ethoxy)dimethylsilane 
• 1150095-72-9 C₁₄H₂₈O₄Si 
• 1566591-28-3 ((4S,5S)-5-(2-(tert-butyldimethylsilyloxy)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol 
• 1566591-26-1 (2-(4S,5S)-5-((benzyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethoxy)(tert-butyl)dimethylsilane 
• 562823-71-6 2-((4S,5S)-5-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol 
• 1566591-42-1 (2R,4S)-4-(methoxymethoxy)hex-5-en-2-yl 2-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)acetate 
• 185030-56-2 tert-Butyl-(2-{(4S,5S)-5-[(E)-(3S,5R)-5-(4-methoxy-benzyloxy)-3-methoxymethoxy-hex-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethoxy)-dimethyl-silane 
• 185030-59-5 (3S,4S,5E,7S,9R)-3.4-(dimethylmethylenedioxy)-9-(4-methoxybenzyloxy)-7-(methoxymethoxy)-5-decenal 

Relevant articles and documents

A facile chiral pool synthesis of 9-epi-decarestrictine-D, decarestrictine-D and O

A facile chiral pool total synthesis of 9-epi-decarestrictine-D, decarestrictine-D and O has been achieved from l-(+)-diethyl tartrate. The strategy utilized is conventional and flexible. Wittig homologation and Grubbs ring closing metathesis are the key reactions employed for the synthesis of the title molecules.

Nickel-catalyzed coupling producing (2Z)-2,4-alkadien-1-ols, conversion to (E)-3-alkene-1,2,5-triol derivatives, and synthesis of decarestrictine D

The 3-alkene-1,2,5-triol structure is not only a major framework of biologically important molecules but also a new functional-group-rich unit for synthesis of polyols and sugars. A method furnishing such triol derivatives 8 was developed and successfully applied to synthesis of decarestrictine D (18). First, coupling reaction of the unprotected alcohols 2 with borates 4 was investigated to produce the dienyl alcohols 6 with NiCl2(dppf) in Et2O/THF (5:1) at room temperature. The hydroxyl-group-directed epoxidation of 6 followed by palladium-catalyzed reaction with AcOH (Scheme 1) furnished 3-alkene-1,2,5-triol derivatives 8. Since each step proceeded with high stereo- and regioselectivities, the stereochemistry of 8 has been correlated with the olefin geometry of 6. With the above transformation in mind, synthesis of the full carbon skeleton of decarestrictine D (18) could be designed easily and was completed successfully. Furthermore, a new seco acid 19b with the MOM protective group for the three hydroxyl groups was found to afford macrolide 48 in a yield higher than those reported previously.

Stereoselective synthesis of decarestrictine D from a previously inaccessible (2Z,4E)-alkadienyl alcohol precursor

(Chemical Equation Presented) The core structure of decarestrictine D was constructed by stereoselective oxygenation of (2Z,4E)-alkadienyl alcohol, which could be synthesized by a nickel-catalyzed coupling reaction between the corresponding cis bromide an