(3R,5R,6S)-2-(hydroxymethyl)-6-(methylthio)oxane-3,4,5-triol

Base Information

• Chemical Name: (3R,5R,6S)-2-(hydroxymethyl)-6-(methylthio)oxane-3,4,5-triol
• CAS No.: 155-30-6
• Deprecated CAS: 27072-97-5,27251-92-9,92225-53-1
• Molecular Formula: C7H14O5S
• Molecular Weight: 210.251
• Hs Code.: 2932999099
• Mol file: 155-30-6.mol

Synonyms:methyl 1-thio-beta-D-galactopyranoside;methyl beta-D-thiogalactopyranoside;methyl beta-D-thiogalactoside;methylthiogalactoside;thiomethylgalactoside

Chemical Property of (3R,5R,6S)-2-(hydroxymethyl)-6-(methylthio)oxane-3,4,5-triol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 115-1170C
• Boiling Point: 437.323oC at 760 mmHg
• Flash Point: 218.285oC
• PSA: 115.45000
• Density: 1.505g/cm3
• LogP: -1.85070
• Storage Temp.: −20°C
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 210.05619472
• Heavy Atom Count: 13
• Complexity: 167

Purity/Quality:

98%, ^*data from raw suppliers

Methyl b-D-thiogalactopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSC1C(C(C(C(O1)CO)O)O)O
• Isomeric SMILES: CS[C@H]1[C@@H](C([C@H](C(O1)CO)O)O)O
• Uses: Inhibition of ?glucosidase Inhibition of β-glucosidase. Methyl-β-D-thiogalactoside has been used in a study to analyze inducers of the E.coli lac repressor system. It has also been used in a study that investigated the utilization of lactose by Streptococcus faecalis.

Technology Process of (3R,5R,6S)-2-(hydroxymethyl)-6-(methylthio)oxane-3,4,5-triol

There total 9 articles about (3R,5R,6S)-2-(hydroxymethyl)-6-(methylthio)oxane-3,4,5-triol 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: 82.0%

methyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside (55722-48-0) → methyl 1-thio-β-D-galactopyranoside (155-30-6)

Guidance literature:

With sodium methylate; In methanol; 1.) 20 deg C, 10 min; 2.) 0-4 deg C, 12 h;

DOI:10.1016/0008-6215(88)84110-7

Reference yield:

β-D-galactose peracetate (4163-60-4) → methyl 1-thio-β-D-galactopyranoside (155-30-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 89.2 percent / molecular sieves (4A) / boron trifluoride etherate (BF₃*Et₂O) / CH₂Cl₂ / 1.) 20 deg C, 2 h; 2.) 0-5 deg C, 48 h

2: 82 percent / NaOMe / methanol / 1.) 20 deg C, 10 min; 2.) 0-4 deg C, 12 h

With 4 A molecular sieve; sodium methylate; boron trifluoride diethyl etherate; In methanol; dichloromethane;

DOI:10.1016/0008-6215(88)84110-7

Reference yield:

Acetic acid (2R,3S,4S,5R)-3,5-diacetoxy-2-acetoxymethyl-6-carbamimidoylsulfanyl-tetrahydro-pyran-4-yl ester; hydrobromide (40591-65-9,51224-13-6,51898-28-3,57030-42-9,106818-92-2) → methyl 1-thio-β-D-galactopyranoside (155-30-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 41 percent / 1.) K₂CO₃, 2.) NaHSO₄ / 1.) H₂O

2: CH₃ONa / methanol

With sodium hydrogen sulfate; sodium methylate; potassium carbonate; In methanol;

upstream raw materials:

methyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside

1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose

sodium thiomethoxide

Trimethyl(methylthio)silane

Downstream raw materials:

benzyl O-<(2,3,4,6-tetra-O-(4-methoxybenzyl)-α-D-galactopyranosyl)>-(1<*>3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-acetamido-4,6-di-O-acetyl-2-deoxy-β-D-glucopyranoside

Methyl 2-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside

methyl 3,4-O-isopropylidene-2-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside

methyl 6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

Refernces

• 1、 Prodger, Jeremy C.,Bamford, Mark J.,Gore, Paul M.,Holmes, Duncan S.,Saez, Victoria,Ward, Peter. "Synthesis of a Novel Analogue of Sialyl Lewis X". . p. 2339 - 2342. Retrieved 2007/10/02.
• 2、 Goto, Fumitaka,Ogawa, Tomoya. "SYNTHESIS OF A SULFATED GLYCOPEPTIDE CORRESPONDING TO THE CARBOHYDRATE-PROTEIN LINKAGE REGION OF PROTEOGLYCANS: β-D-GlcA-(1->3)4)>-β-D-Gal-(1->3)-β-D-Gal-(1->4)-β-D-Xyl-(1->3)-Ser". . p. 5099 - 5102. Retrieved 2007/10/02.