Nonyl beta-D-thioglucopyranoside

Base Information

• Chemical Name: Nonyl beta-D-thioglucopyranoside
• CAS No.: 98854-15-0
• Molecular Formula: C₁₅H₃₀O₅S
• Molecular Weight: 322.466
• Hs Code.: 2932999099
• European Community (EC) Number: 664-063-1
• DSSTox Substance ID: DTXSID10470659
• Wikidata: Q72496658
• Mol file: 98854-15-0.mol

Synonyms:Nonyl b-D-thioglucopyranoside;Nonyl beta-D-thioglucopyranoside;98854-15-0;(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-nonylsulfanyloxane-3,4,5-triol;Nonyl 1-thiohexopyranoside #;SCHEMBL416020;DTXSID10470659;HICSQFRUQXWIGI-QMIVOQANSA-N;Nonyl 1-thio-beta-D-glucopyranoside;.beta.-d-Glucopyranoside, nonyl 1-thio-;Nonyl-beta-D-thioglucoside, >=99% (TLC);W-204177;(2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(nonylthio)tetrahydro-2H-pyran-3,4,5-triol

Chemical Property of Nonyl beta-D-thioglucopyranoside

Chemical Property:

• PSA: 115.45000
• LogP: 1.27010
• Storage Temp.: 2-8°C
• Solubility.: methanol: water (1:1): soluble0.05%, clear, colorless
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 322.18139523
• Heavy Atom Count: 21
• Complexity: 266

Purity/Quality:

98%,99%, ^*data from raw suppliers

Nonyl b-D-thioglucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCCCCCSC1C(C(C(C(O1)CO)O)O)O
• Isomeric SMILES: CCCCCCCCCS[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O

Technology Process of Nonyl beta-D-thioglucopyranoside

There total 9 articles about Nonyl beta-D-thioglucopyranoside 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:

n-nonyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (98854-13-8) → n-nonyl-β-D-thioglucopyranoside (98854-15-0)

Guidance literature:

With sodium hydroxide; In methanol; Ambient temperature;

Reference yield:

Nonane-1-thiol (1455-21-6) + β-D-glucose pentaacetate (604-69-3) → n-nonyl-β-D-thioglucopyranoside (98854-15-0)

Guidance literature:

Multi-step reaction with 2 steps

1: boron trifluoride diethyl etherate

2: sodium methylate / methanol

With boron trifluoride diethyl etherate; sodium methylate; In methanol;

DOI:10.1016/j.molliq.2018.11.134

Reference yield:

1-Bromononane (693-58-3) → n-nonyl-β-D-thioglucopyranoside (98854-15-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / K₂CO₃, NaHSO₃ / acetone; H₂O / Ambient temperature

2: NaOH / methanol / Ambient temperature

With sodium hydroxide; potassium carbonate; sodium hydrogensulfite; In methanol; water; acetone;

upstream raw materials:

n-nonyl 2,3,4,6-tetra-O-acetyl-1-thio-D-glucopyranoside

D-glucose pentaacetate

Nonane-1-thiol

n-nonyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside

Refernces

• 1、 Dahlhoff, Wilhelm V.. "Ampiphilic Carbohydrate-Based Mesogens, VI: Synthesis of a Series of Alkyl 1-Thio-D-glucopyranosides and Their Regioselective Reductions to 1-Alkylthio-1-deoxy-D-glucitols". . p. 1025 - 1027. Retrieved 2007/10/02.