(-)-1,4-Di-O-methyl-L-threitol

Base Information

• Chemical Name: (-)-1,4-Di-O-methyl-L-threitol
• CAS No.: 50622-10-1
• Molecular Formula: C6H14O4
• Molecular Weight: 150.17
• Hs Code.: 2909499000
• DSSTox Substance ID: DTXSID30448698
• Nikkaji Number: J47.386C
• Wikidata: Q63399030
• Mol file: 50622-10-1.mol

Synonyms:(-)-1,4-Di-O-methyl-L-threitol;50622-10-1;(2s,3s)-1,4-dimethoxybutane-2,3-diol;(S,S)-(-)-1,4-Dimethoxy-2,3-butanediol;1,4-Di-O-methyl-L-threitol;1-O,4-O-Dimethyl-L-threitol;DTXSID30448698;MFCD00077736;AT25369;(2S,3S)-(-)-1,4-dimethoxy-2,3-butanediol;(2S,3S)-1,4-DIMETHOXY-2,3-BUTANEDIOL;J-501026;Q63399030;(S,S)-(-)-1,4-Dimethoxy-2,3-butanediol, >=99.0% (sum of enantiomers, GC)

Chemical Property of (-)-1,4-Di-O-methyl-L-threitol

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 28-30 °C
• Refractive Index: 1.447
• Boiling Point: 263.751°C at 760 mmHg
• PKA: 13.27±0.20(Predicted)
• Flash Point: 113.313°C
• PSA: 58.92000
• Density: 1.104g/cm³
• LogP: -0.99900
• Storage Temp.: 2-8°C
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 150.08920892
• Heavy Atom Count: 10
• Complexity: 66.1

Purity/Quality:

98%Min ^*data from raw suppliers

(S,S)-(?)-1,4-Dimethoxy-2,3-butanediol ≥99.0% (sum of enantiomers, GC) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COCC(C(COC)O)O
• Isomeric SMILES: COC[C@@H]([C@H](COC)O)O

Technology Process of (-)-1,4-Di-O-methyl-L-threitol

There total 7 articles about (-)-1,4-Di-O-methyl-L-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: 99.0%

(S,S)-(-)-4,5-Bis(methoxymethyl)-2,2-dimethyl-1,3-dioxolan (51064-64-3) → (-)-(2S,3S)-1,4-dimethoxy-2,3-butanediol (50622-10-1)

Guidance literature:

With hydrogenchloride; water; In methanol; at 20 ℃; for 2h;

DOI:10.1002/chir.22678

Reference yield: 90.0%

1,4-di-O-methyl-2,3-di-O-(tetrahydropyran-2-yl)-L-threitol (123612-41-9) → (-)-(2S,3S)-1,4-dimethoxy-2,3-butanediol (50622-10-1)

Guidance literature:

With 2 .) Dowex IRA 400 (OH^(1-) form); trifluoroacetic acid; In methanol; water; 1.) overnight, 2.) 1 h;

Reference yield: 89.2%

{(R)-[2-((4S,5S)-4,5-Bis-methoxymethyl-[1,3]dioxolan-2-ylmethyl)-phenyl]-phenyl-methyl}-carbamic acid benzyl ester → (-)-(2S,3S)-1,4-dimethoxy-2,3-butanediol (50622-10-1) + (R)-(+)-benzyl 1-phenyl-1,2-dihydroisoquinoline-2-carboxylate (207615-49-4)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 65 ℃; for 16h;

DOI:10.1002/(SICI)1099-0690(199804)1998:4<711::AID-EJOC711>3.0.CO;2-A

upstream raw materials:

(S,S)-(-)-4,5-Bis(methoxymethyl)-2,2-dimethyl-1,3-dioxolan

(4R)-4r,5t-bis-methoxymethyl-2,2-dimethyl-[1,3]dioxolane

methanol

(S,S)-diepoxybutane

Downstream raw materials:

(4S,5S)-4,5-Bis-methoxymethyl-2-methyl-2-o-tolyl-[1,3]dioxolane

(4S,5S)-2-(2-Bromo-benzyl)-4,5-bis-methoxymethyl-[1,3]dioxolane

(4S)-4-<(4S,5S)-4,5-dimethoxymethyl-2-methyl-1,3-dioxolan-2-yl>-1-p-methoxyphenyl-2-azetidinone

(4R)-4-<(4S,5S)-4,5-dimethoxymethyl-2-methyl-1,3-dioxolan-2-yl>-1-p-methoxyphenyl-3,3-dimethyl-2-azetidinone

Refernces

• 1、 Koba, Yurie,Ueda, Atsushi,Oba, Makoto,Doi, Mitsunobu,Kato, Takuma,Demizu, Yosuke,Tanaka, Masakazu. "Left-Handed Helix of Three-Membered Ring Amino Acid Homopeptide Interrupted by an N-H···Ethereal O-Type Hydrogen Bond". supporting information. p. 7830 - 7834. Retrieved 2018/12/14.
• 2、 Lee, Yong Sup,Seo, Seon Hee,Yang, Beom-Seok,Lee, Jae Yeol. "Synthesis and biological evaluation of bis(methoxy-methyl)-7,8-dihydro-[1, 4]dioxino[2,3-g]quinazolines as EGFR tyrosine kinase inhibitors". . p. 502 - 505. Retrieved 2007/10/03.