(-)-2,3-O-Isopropylidene-d-threitol

Base Information

• Chemical Name: (-)-2,3-O-Isopropylidene-d-threitol
• CAS No.: 73346-74-4
• Molecular Formula: C7H14O4
• Molecular Weight: 162.186
• Hs Code.: 29329970
• European Community (EC) Number: 277-391-1
• Nikkaji Number: J208.646H
• Wikidata: Q106892303
• Mol file: 73346-74-4.mol

Synonyms:73346-74-4;(-)-2,3-O-Isopropylidene-d-threitol;((4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)dimethanol;2,3-o-isopropylidene-d-threitol;trans-((4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)dimethanol;[(4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol;86992-57-6;1,3-Dioxolane-4,5-dimethanol, 2,2-dimethyl-, (4R,5R)-;(4R,5R)-4,5-Bis(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane;MFCD00009761;[(4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl]dimethanol;EINECS 277-391-1;D-(-)-2,2-Dimethyl-1,3-dioxolane-4,5-dimethanol;SCHEMBL560668;(4R,5R)-(-)-2,2-Dimethyl-1,3-dioxolane-4,5-dimethanol;2-O,3-O-Isopropylidene-D-threitol;AKOS016843666;(-)-2-3-O-Isopropylidene-D-threitol;AS-49892;(-)-2,3-Di-O-isopropylidene-D-threitol;CS-0097521;I0375;(-)-2,3-O-Isopropylidene-D-threitol, 99%;O10001;A837797;W-203672;1,3-Dioxolane-4,5-dimethanol,2,2-dimethyl-, (4R,5R)-;(4R-trans)-(-)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol;(4R,5R)-(-)-4,5-Bis(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane;[(4R,5R)-5-Hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]methanol;((4R,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol

Chemical Property of (-)-2,3-O-Isopropylidene-d-threitol

Chemical Property:

• Appearance/Colour: colorless to light yellow liquid
• Vapor Pressure: 8.03E-06mmHg at 25°C
• Melting Point: 48-51 °C(lit.)
• Refractive Index: -4 ° (C=5, Acetone)
• Boiling Point: 335.9 °C at 760 mmHg
• PKA: 13.90±0.10(Predicted)
• Flash Point: 111.9 °C
• PSA: 58.92000
• Density: 1.108 g/cm³
• LogP: -0.50890
• Storage Temp.: 0-6°C
• Sensitive.: Hygroscopic
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate, THF
• Water Solubility.: Soluble in water.
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 162.08920892
• Heavy Atom Count: 11
• Complexity: 120

Purity/Quality:

99% ^*data from raw suppliers

2,3-Di-O-isopropylidene-D-threitol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC(C(O1)CO)CO)C
• Isomeric SMILES: CC1(O[C@@H]([C@H](O1)CO)CO)C
• Uses: (-)-2,3-O-Isopropylidene-D-threitol is used in the synthesis of the optically active enantiomorphic 2,3-butanediols (-)-2,3-O-Isopropylidene-D-threitol is used in the synthesis of the optically active enantiomorphic 2,3-butanediols. It react with toluene-4-sulfonyl chloride to get O2,O3-isopropylidene-O1,O4-bis-(toluene-4-sulfonyl)-D-threitol.

Technology Process of (-)-2,3-O-Isopropylidene-d-threitol

There total 18 articles about (-)-2,3-O-Isopropylidene-d-threitol 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: 100.0%

(+)-dimethyl-2,3-O-isopropylidene-D-tartrate (37031-29-1,6134-82-3,6135-80-4,90613-41-5,116499-08-2,37031-30-4) → (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol (73346-74-4)

Guidance literature:

With methanol; sodium tetrahydroborate;

DOI:10.1002/chir.22814

Reference yield: 92.0%

(4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (73346-73-3) → (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol (73346-74-4)

Guidance literature:

With sodium tetrahydroborate; lithium chloride; In tetrahydrofuran; ethanol; at 20 ℃; for 14h;

DOI:10.1016/j.tetlet.2019.151085

Reference yield: 90.0%

diisopropyl (2S,3S)-2,3-O-isopropylidenetartrate (81327-47-1,121668-38-0) → (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol (73346-74-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1016/j.tetlet.2014.02.096

upstream raw materials:

3,4-di-O-isopropylidene-D-mannitol

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

(4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

(4R)-3,4-(isopropylidenedioxy)tetrahydrofuran-2-ol

Downstream raw materials:

1,4-di-o-tosyl-2,3-isopropylidene-D-threitol

[(4R,5R)-5-((S)-5,7-Bis-benzyloxy-heptyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol

[(4R,5R)-5-((S)-5,7-Bis-benzyloxy-hept-2-ynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol

(4R,5R)-4-((S)-5,7-Bis-benzyloxy-heptyl)-5-but-3-enyl-2,2-dimethyl-[1,3]dioxolane

Refernces

• 1、 Ohira, Susumu,Kuboki, Atsuhito,Takimoto, Yoshimi,Matsuda, Kyosuke,Itasaki, Saori,Urushibata, Yuki,Takano, Yoshiyuki,Nakamura, Yuuki. "Novel protection of 1,2-diol for trans-dihydroxycyclopentene ring construction by the C[sbnd]H insertion of alkylidene carbene: Formal total synthesis of (+)-trehazolin". . . Retrieved 2019/09/03.
• 2、 Mallavadhani, Uppuluri Venkata,Boddu, Ramakrishna,Rathod, Balaji B.,Reddy Setty, Prakasam. "Stereoselective synthesis of the lichen metabolite, (+) montagnetol and its congeners as antimicrobial agents". supporting information. p. 2992 - 2999. Retrieved 2018/10/15.