(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

Base Information

• Chemical Name: (4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
• CAS No.: 13039-94-6
• Molecular Formula: C11H18 O5
• Molecular Weight: 230.261
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID901262204
• Nikkaji Number: J1.997.214C
• Mol file: 13039-94-6.mol

Synonyms:13039-94-6;(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde;(4S,4'R,5R)-2,2,2',2'-Tetramethyl-[4,4'-bi(1,3-dioxolane)]-5-carbaldehyde;SCHEMBL9699787;VFGWJIQTAFPNQZ-DJLDLDEBSA-N;DTXSID901262204;AMY24704;2-O,3-O:4-O,5-O-Diisopropylidene-D-xylose;2,3:4,5-Bis-O-(1-methylethylidene)-D-xylose

Chemical Property of (4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

Chemical Property:

• Boiling Point: 289.5±40.0 °C(Predicted)
• PSA: 46.15000
• Density: 1.159±0.06 g/cm3(Predicted)
• LogP: 1.01430
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 230.11542367
• Heavy Atom Count: 16
• Complexity: 286

Purity/Quality:

99% ^*data from raw suppliers

2,3,4,5-DI-O-ISOPROPYLIDENE-D-XYLOSE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

There total 15 articles about (4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde 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: 98.1%

2,3:4,5-di-O-isopropylidene-D-xylose di(p-tolyl) dithioacetal → 2,3,4,5-di-O-isopropylidene-D-xylose aldehyde (13039-94-6)

Guidance literature:

With mercury dichloride; mercury(II) oxide; In water; acetone; at 55 ℃; for 12h;

DOI:10.1016/j.bmc.2014.08.002

Reference yield: 97.0%

2,3:4,5-di-D-isopropylidene-D-xylose diethyl dithioacetal (3673-14-1) → 2,3,4,5-di-O-isopropylidene-D-xylose aldehyde (13039-94-6)

Guidance literature:

With boron trifluoride diethyl etherate; mercury(II) oxide; In tetrahydrofuran; water; for 1h;

Reference yield: 92.0%

2,3,4,5-di-O-isopropylidene-D-xylitol (30737-85-0) → 2,3,4,5-di-O-isopropylidene-D-xylose aldehyde (13039-94-6)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 18 ℃; for 1.5h;

DOI:10.1055/s-1999-3179

upstream raw materials:

D-Xylose

2-Methoxypropene

(4S,4'R,5S)-2,2,2',2'-tetramethyl-[4,4'-bi(1,3-dioxolane)]-5-carbaldehyde

Acetic acid phenylsulfanyl-((4S,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl ester

Downstream raw materials:

(1R)-1-(2,4-bis-benzyloxy-pyrimidin-5-yl)-O²,O³;O⁴,O⁵-diisopropylidene-D-xylitol

5,5-dimethyl-imidazolidine-2,4-dione

5-(D-threo-2,3,4-trihydroxybutylidene)imidazol-2,4-dione

5-(D-erythro-2-hydroxy-3,4-isopropylidenedioxybutylidene)imidazol-2,4-dione

Refernces

• 1、 Kumar, Rayala Naveen,Meshram. "Convergent and stereoselective synthesis of (-)-zeaenol". . p. 5669 - 5677. Retrieved 2015/08/03.
• 2、 Long, David E.,Karmakar, Partha,Wall, Katherine A.,Sucheck, Steven J.. "Synthesis of α-l-rhamnosyl ceramide and evaluation of its binding with anti-rhamnose antibodies". . p. 5279 - 5289. Retrieved 2014/12/11.