91604-41-0

Basic information

• Product Name: (+)-1,4-DI-O-BENZYL-D-THREITOL
• Synonyms: (+)-1,4-DI-O-BENZYL-D-THREITOL;1,4-DI-O-BENZYL-D-THREITOL;(+)-(2R,3R)-1,4-BIS(BENZYLOXY)-2,3-BUTANEDIOL;(2R,3R)-(+)-1,4-DIBENZYLOXY-2,3-BUTANEDIOL;Dibenzylthreitol;(+)-1,4-Di-O-benzyl-D-threito;2,3-BUTANEDIOL, 1,4-BIS(PHENYLMETHOXY)-, (2R,3R)-;1,4-dibenzyloxy-2,3-butanediol
• CAS NO: 91604-41-0
• Molecular Formula: C₁₈H₂₂O₄
• Molecular Weight: 302.36
• Product Categories: chiral;Asymmetric Synthesis;Biochemistry;Chiral Building Blocks;Simple Alcohols (Chiral);Sugar Alcohols;Sugars;Synthetic Organic Chemistry
• Mol File: 91604-41-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 55-58 °C
• Boiling Point: 484.4 °C at 760 mmHg
• Flash Point: 246.7 °C
• Appearance: /
• Density: 1.174 g/cm³
• Vapor Pressure: 3.41E-10mmHg at 25°C
• Refractive Index: 6.3 ° (C=5, CHCl3)
• Solubility: almost transparency in Chloroform
• BRN: 3557415
• CAS DataBase Reference: (+)-1,4-DI-O-BENZYL-D-THREITOL(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-1,4-DI-O-BENZYL-D-THREITOL(91604-41-0)
• EPA Substance Registry System: (+)-1,4-DI-O-BENZYL-D-THREITOL(91604-41-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 91604-41-0(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

InChI:InChI=1/C18H22O4/c19-17(13-21-11-15-7-3-1-4-8-15)18(20)14-22-12-16-9-5-2-6-10-16/h1-10,17-20H,11-14H2/t17-,18-/m1/s1

Upstream product

• 68972-93-0 (E)-1,4-bis(benzyloxy)-2-butene 
• 91604-40-9 1,4-di-O-benzyl-2,3-O-isopropylidene-D-threitol 
• 102521-17-5 (1S,15S)-bicyclo<13.1.0>hexadecan-2-one 1,4-di-O-benzyl-D-threitol ketal 
• 100-39-0 benzyl bromide 
• 1472686-48-8 (2R,3R)-1,4-di-O-benzyl-2,3-O-(3-pentylidene)threitol 
• 97-72-3 2-Methylpropionic anhydride 
• 14679-55-1 DL-1,4-Dibenzyloxy-2,3-butandiol 
• 564-00-1 meso-1,2,3,4-diepoxybutane 
• 100-51-6 benzyl alcohol 

Downstream Products

• 144405-27-6 (4R,5R)-4,5-dibenzoyloxymethyl-2-methoxycarbonyl-2-phenyl-1,3-dioxolane 
• 88454-94-8 C₃₆H₅₄O₁₀ 
• 116948-59-5 (2R,3R)-2,3-Bis-benzyloxymethyl-1,4-dioxa-spiro[4.4]non-6-ene 
• 83892-80-2 (S,S)-1,2-Bis<(benzyloxy)methyl>-15-krone-5 
• 102572-90-7 (1R,15R)-bicyclo<13.1.0>hexadecan-2-one 1,4-di-O-benzyl-D-threitol ketal 
• 102521-17-5 (1S,15S)-bicyclo<13.1.0>hexadecan-2-one 1,4-di-O-benzyl-D-threitol ketal 
• 156386-42-4 2-bromomethyl-4(R),5(R)-dibenzyloxymethyl-1,3-dioxolane 
• 178453-40-2 1,4-Di-O-benzyl-2,3-di-O-octyl-D-threitol 
• 178453-41-3 1,4-Di-O-benzyl-2,3-di-O-decyl-D-threitol 
• 178453-42-4 1,4-Di-O-benzyl-2,3-di-O-dodecyl-D-threitol 
• 181045-86-3 (2R,3R)-1,4-Bis-benzyloxy-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-butan-2-ol 
• 167937-19-1 (2R,3R)-1,4-dibenzyloxy-2,3-dimethanesulfonyloxybutane 

Relevant articles and documents

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

The chiral vicinal diol was protected as 6-methylene-1,4-dioxepane to construct a cyclopentene ring by the C[sbnd]H insertion of alkylidene carbene. The removal of the protecting group was achieved in a few steps, affording the corresponding diol in a reasonable yield. Using these reactions, the known synthetic intermediate for (+)-trehazolin was synthesized from D-diethyl tartrate. In addition, a short route to the intermediate from a D-mannitol derivative was described.

An optimized synthetic route for the preparation of the versatile chiral building block 1,4-di-O-benzylthreitol

An improved five-step procedure has been applied to synthesize enantiopure l- and d-1,4-di-O-benzylthreitol out of readily available l- and d-tartaric acid. Through the use of modern reagents and enhanced work-up conditions these useful auxiliaries were o

Enanthioselective Phase-Transfer Catalysis by Optically Active Crown Ethers

1,2-Bis(hydroxymethyl)-15-crown-5 (1a), its dibenzyl ether (1b), and a series of esters with substituted benzoic acid (3) were probed as enanthioselective phase-transfer catalysts.Optical yields were observed in epoxidations of unsaturated ketones by hypochlorite and in cyanide additions to such compounds.The maximum ee value was 45percent.Polar side groups of the optically active crown ethers proved to be vital for enanthiomeric excesses.