(3R,4S)-3-[(4R)-2,2-Dimethyl-1,3-dioxolan-4-YL]-7,7-dimethyl-4-prop-2-enoxy-2,6,8-trioxabicyclo[3.3.0]octane

Base Information

• Chemical Name: (3R,4S)-3-[(4R)-2,2-Dimethyl-1,3-dioxolan-4-YL]-7,7-dimethyl-4-prop-2-enoxy-2,6,8-trioxabicyclo[3.3.0]octane
• CAS No.: 20316-77-2
• Molecular Formula: C15H24O6
• Molecular Weight: 300.352
• DSSTox Substance ID: DTXSID601153189
• Nikkaji Number: J516.227K
• Mol file: 20316-77-2.mol

Synonyms:20316-77-2;(3R,4S)-3-[(4R)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YL]-7,7-DIMETHYL-4-PROP-2-ENOXY-2,6,8-TRIOXABICYCLO[3.3.0]OCTANE;(4R)-4-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-(prop-2-en-1-yloxy)-tetrahydro-2H-furo[2,3-d][1,3]dioxol-5-yl]-2,2-dimethyl-1,3-dioxolane;SCHEMBL8872590;DTXSID601153189;3-O-Allyl-1-O,2-O:5-O,6-O-diisopropylidene-alpha-D-glucofuranose;1,2:5,6-Bis-O-(1-methylethylidene)-3-O-2-propen-1-yl-|A-D-glucofuranose;3-O-Allyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose, Min. 98%;1,2:5,6-Bis-O-(1-methylethylidene)-3-O-2-propen-1-yl-alpha-D-glucofuranose

Chemical Property of (3R,4S)-3-[(4R)-2,2-Dimethyl-1,3-dioxolan-4-YL]-7,7-dimethyl-4-prop-2-enoxy-2,6,8-trioxabicyclo[3.3.0]octane

Chemical Property:

• Vapor Pressure: 6.5E-05mmHg at 25°C
• Boiling Point: 355.2°Cat760mmHg
• Flash Point: 139.6°C
• PSA: 55.38000
• Density: 1.17g/cm³
• LogP: 1.58550
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 300.15728848
• Heavy Atom Count: 21
• Complexity: 407

Purity/Quality:

99%, ^*data from raw suppliers

3-O-Allyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose 98%min ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OCC(O1)C2C(C3C(O2)OC(O3)(C)C)OCC=C)C
• Isomeric SMILES: CC1(OC[C@@H](O1)[C@@H]2[C@@H]([C@@H]3[C@H](O2)OC(O3)(C)C)OCC=C)C

Technology Process of (3R,4S)-3-[(4R)-2,2-Dimethyl-1,3-dioxolan-4-YL]-7,7-dimethyl-4-prop-2-enoxy-2,6,8-trioxabicyclo[3.3.0]octane

There total 22 articles about (3R,4S)-3-[(4R)-2,2-Dimethyl-1,3-dioxolan-4-YL]-7,7-dimethyl-4-prop-2-enoxy-2,6,8-trioxabicyclo[3.3.0]octane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

allyl bromide (106-95-6) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → (3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole (20316-77-2)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; for 24h;

DOI:10.1021/ol027288c

Reference yield: 95.0%

allyl iodid (556-56-9) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → (3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole (20316-77-2)

Guidance literature:

With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 4h; Inert atmosphere;

DOI:10.2174/1570178614666170307091943

Reference yield: 95.0%

3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose (16713-80-7) + allyl bromide (106-95-6) → (3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole (20316-77-2)

Guidance literature:

With sodium hydroxide; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1016/j.carres.2005.03.007

upstream raw materials:

Natrium-Verbindung der O¹,O²;O⁵,O⁶-Diisopropyliden-α-D-glucofuranose

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

allyl bromide

3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose

Downstream raw materials:

acetyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside

Bis-{3-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-propyl}-phenyl-phosphane

³O-(3-diphenylphosphinopropyl)-¹O,²O:⁵O,⁶O-diisopropylideneglucofuranose

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

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