17401-06-8

Basic information

• Product Name: (-)-1,4-DI-O-BENZYL-L-THREITOL
• Synonyms: (-)-1,4-DI-O-BENZYL-L-THREITOL;1,4-DI-O-BENZYL-L-THREITOL;(-)-(2S,3S)-1,4-BIS(BENZYLOXY)-2,3-BUTANEDIOL;(2S,3S)-(-)-1,4-DIBENZYLOXY-2,3-BUTANEDIOL;(-)-1,4-DI-O-BENZYL-L-THREITOL 98+%;2,3-BUTANEDIOL, 1,4-BIS(PHENYLMETHOXY)-, (2S,3S)-;(-)-1,4-Di-O-benzyl-L-threitol, 1,4-Di-O-benzyl-L-threitol, (-)-(2S,3S)-1,4-Bis(benzyloxy)-2,3-butanediol;1-O,4-O-Dibenzyl-L-threitol
• CAS NO: 17401-06-8
• 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: 17401-06-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 55-58 °C
• Boiling Point: 484.4 °C at 760 mmHg
• Flash Point: 246.7 °C
• Appearance: white to light yellow crystal powder
• Density: 1.174 g/cm³
• Vapor Pressure: 3.41E-10mmHg at 25°C
• Refractive Index: -6.3 ° (C=5, CHCl3)
• Storage Temp.: 2-8°C
• Solubility: almost transparency in Chloroform
• PKA: 13.24±0.20(Predicted)
• BRN: 2149394
• CAS DataBase Reference: (-)-1,4-DI-O-BENZYL-L-THREITOL(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-1,4-DI-O-BENZYL-L-THREITOL(17401-06-8)
• EPA Substance Registry System: (-)-1,4-DI-O-BENZYL-L-THREITOL(17401-06-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 17401-06-8(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-/m0/s1

Upstream product

• 75-11-6 diiodomethane 
• 99249-28-2 2-cyclohexen-1-one cyclic (1S,2S)-1,2-bis<(benzyloxy)methyl>ethylene acetal 
• 564-00-1 meso-1,2,3,4-diepoxybutane 
• 100-51-6 benzyl alcohol 
• 97-72-3 2-Methylpropionic anhydride 
• 14679-55-1 DL-1,4-Dibenzyloxy-2,3-butandiol 
• 1472686-46-6 (2S,3S)-1,4-di-O-benzyl-2,3-O-(3-pentylidene)threitol 
• 119884-54-7 (2S,3S)-2,3-bis[(benzyloxy)methyl]-1,4-dioxaspiro[4.4]nonane 
• 1160725-28-9 (2S,3S)-1,4-dibenzyloxy-2,3-butandiyl bis(4-O-benzylgallate) 
• 1048381-21-0 C₂₄H₃₂O₆ 
• 100-44-7 benzyl chloride 
• 131846-17-8 4',5'-bis(benzyloxymethyl)bicyclo<3.2.0>hept-2-ene-6-spiro-2'-(1',3'-dioxolane) 
• 100-39-0 benzyl bromide 
• 131846-18-9 1S,2R,3R,5S,4'S,5'S-2-bromo-3-hydroxy-4',5'-bis(benzyloxymethyl)bicyclo<3.2.0>heptane-6-spiro-2'-(1',3'-dioxolane) 

Downstream Products

• 109908-38-5 2-methyl-2-cyclopenten-1-one cyclic (1S,2S)-1,2-bis<(benzyloxy)methyl>ethylene acetal 
• 105543-55-3 3,4,5,6,7,8-hexahydronaphtalen-1(2H)-one cyclic (1S,2S)-1,2-bis<(benzyloxy)methyl>ethylene acetal 
• 105543-61-1 2,3,5,6,7,8-hexahydro-1H,4H-azulen-1-one cyclic (1S,2S)-1,2-bis-<(benzyloxy)methyl>ethylene acetal 
• 105543-59-7 2,3,4,5,6,7-hexahydro-1H-inden-1-one cyclic (1S,2S)-1,2-bis<(benzyloxy)methyl>ethylene acetal 
• 99249-37-3 3-cyclohexen-1-one cyclic (1S,2S)-1,2-bis-<(benzyloxy)methyl>ethylene acetal 
• 99249-44-2 methyl (E)-6-formyl-5-hexenoate cyclic (1S,2S)-1,2-bis<(benzyloxy)methyl>ethylene acetal 
• 102521-15-3 (E)-cyclopentadec-2-en-1-one cyclic (1S,2S)-1,2-bis<(benzyloxy)methyl>ethylene acetal 
• 67654-49-3 (+)-(2S,3S)-2,3-bis(benzyloxymethyl)-1,4,7,10,13,16-hexaoxacyclooctadecane 
• 126277-52-9 (2S,3S)-(-)-2,3-bis(benzyloxymethyl)-1,4,8,11-tetraoxacyclotetradecane 
• 88454-94-8 1,4-Di-O-benzyl-2,3-bis-O-<2-<2-(2-tetrahydropyranyloxy)ethoxy>ethyl>-L-threitol 
• 123292-06-8 (19S,20S)-19,20-bis((phenylmethoxy)methyl)-27,28,29,30-tetraethoxy-18,21-dioxapentacyclo<21.3.1.1^2,6.1^7,11.1^12,16>triaconta-1(27),2,4,6(30),7,9,11(29),12,14,16(28),23,25-dodecaene 
• 83892-78-8 (S,S,S,S)-1,2,7,8-Tetrakis-12-crown-4 
• 123292-09-1 (+)-(19S,20S)-19,20-bis((phenylmethoxy)methyl)-27,28,29,30-tetrakis(phenylmethoxy)-18,21-dioxapentacyclo<21.3.1.1^2,6.1^7,11.1^12,16>triaconta-1(27),2,4,6(30),7,9,11(29),12,14,16(28),23,25-dodecaene 
• 145312-99-8 (1S,2R,3R,5R,4'S,5'S)-2-bromo-3-hydroxy-4',5'-bis(benzyloxymethyl)spirooctane-7,2'(1,3)-dioxolane> 

Relevant articles and documents

Synthesis of l-threitol-based crown ethers and their application as enantioselective phase transfer catalyst in Michael additions

A few new l-threitol-based lariat ethers incorporating a monoaza-15-crown-5 unit were synthesized starting from diethyl l-tartrate. These macrocycles were used as phase transfer catalysts in asymmetric Michael addition reactions under mild conditions to afford the adducts in a few cases in good to excellent enantioselectivities. The addition of 2-nitropropane to trans-chalcone, and the reaction of diethyl acetamidomalonate with β-nitrostyrene resulted in the chiral Michael adducts in good enantioselectivities (90% and 95%, respectively). The substituents of chalcone had a significant impact on the yield and enantioselectivity in the reaction of diethyl acetoxymalonate. The highest enantiomeric excess (ee) values (99% ee) were measured in the case of 4-chloro- and 4-methoxychalcone. The phase transfer catalyzed cyclopropanation reaction of chalcone and benzylidene-malononitriles using diethyl bromomalonate as the nucleophile (MIRC reaction) was also developed. The corresponding chiral cyclopropane diesters were obtained in moderate to good (up to 99%) enantioselectivities in the presence of the threitol-based crown ethers.

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

Synthesis of chiral and modifiable hexahydroxydiphenoyl compounds

A reliable method for synthesizing each enantiomer of the hexahydroxydiphenoyl (HHDP) compounds has been developed. The synthesis involved atropselective construction of the aryl - aryl bond of the HHDP compounds. This construction relied on the CuCl2·n-BuNH2-mediated intramolecular coupling of bis(4-O-benzylgallate) on two simple chiral auxiliaries, both of which were derived from l-(+)-tartaric acid. The coupling reaction realized complete or near-perfect atropselectivity. The two auxiliaries induced opposite axial chirality despite their identical origin. The diastereoselectivities of these couplings were probably controlled kinetically. Modifications of the free phenolic hydroxy groups and the carbonyl groups in the resulting HHDP compounds demonstrated the potential derivatization of a wide variety of HHDP analogues.