(2S,3R,4S,5S,6R)-2-(Decylthio)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Base Information

• Chemical Name: (2S,3R,4S,5S,6R)-2-(Decylthio)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• CAS No.: 98854-16-1
• Molecular Formula: C16H32O5S
• Molecular Weight: 336.48700
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID50469188
• Nikkaji Number: J3.496.654K
• Wikidata: Q72461768
• Mol file: 98854-16-1.mol

Synonyms:98854-16-1;Decyl beta-D-thioglucopyranoside;(2S,3R,4S,5S,6R)-2-(Decylthio)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;Decyl b-D-thioglucopyranoside;Decyl-beta-D-1-thioglucopyranoside;(2S,3R,4S,5S,6R)-2-decylsulfanyl-6-(hydroxymethyl)oxane-3,4,5-triol;Decyl 1-thiohexopyranoside #;Decyl-|A-D-1-thioglucopyranoside;decyl-beta-d-thioglucopyranoside;SCHEMBL1666664;DTXSID50469188;WXUWOACRYZHYQL-LJIZCISZSA-N;Decyl-1-thio-I(2)-D-glucopyranoside;CS-W021042;.beta.-d-Glucopyranoside, decyl 1-thio-;C16864;A858511;W-204178

Chemical Property of (2S,3R,4S,5S,6R)-2-(Decylthio)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Chemical Property:

• PSA: 115.45000
• LogP: 1.66020
• Storage Temp.: −20°C
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 336.19704529
• Heavy Atom Count: 22
• Complexity: 279

Purity/Quality:

98%, ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCCCCCCSC1C(C(C(C(O1)CO)O)O)O
• Isomeric SMILES: CCCCCCCCCCS[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• Uses: Decyl b-D-thioglucopyranoside

Technology Process of (2S,3R,4S,5S,6R)-2-(Decylthio)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

There total 10 articles about (2S,3R,4S,5S,6R)-2-(Decylthio)-6-(hydroxymethyl)tetrahydro-2H-pyran-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: 77.0%

1-thio-β-D-glucopyranose (22566-82-1,23558-19-2,49858-49-3,63073-99-4,135891-42-8,7534-35-2) + 1-Decene (872-05-9,17438-89-0,25189-70-2) → n-Decyl 1-thio-β-D-glucopyranoside (98854-16-1)

Guidance literature:

With 2,2-dimethoxy-2-phenylacetophenone; In methanol; at 20 - 25 ℃; for 0.5h; Solvent; UV-irradiation;

DOI:10.3762/bjoc.15.90

Reference yield:

n-decyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (98854-14-9) → n-Decyl 1-thio-β-D-glucopyranoside (98854-16-1)

Guidance literature:

With sodium hydroxide; In methanol; Ambient temperature;

Reference yield:

decylthiol (143-10-2) + β-D-glucose pentaacetate (604-69-3) → n-Decyl 1-thio-β-D-glucopyranoside (98854-16-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: indium(III) bromide / chloroform / Reflux

2.1: sodium methylate / methanol / 16 h / pH 9

2.2: dowex^? resin (H⁺ form)

With indium(III) bromide; sodium methylate; In methanol; chloroform;

DOI:10.1016/j.carres.2015.12.008

upstream raw materials:

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

D-glucose pentaacetate

decylthiol

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

Refernces

• 1、 Wu, Xiubing,Chen, Langqiu,Fu, Fang,Fan, Yulin,Luo, Zhiqiang. "Synthesis and surface properties of alkyl β?D?thioglucopyranoside". . p. 282 - 289. Retrieved 2018/12/13.
• 2、 Smits,Engberts,Kelogg,Van Doren. "Non-amphiphilic carbohydrate liquid crystals containing an intact monosaccharide moiety". . p. 185 - 199. Retrieved 2007/10/02.