(2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(isopropylthio)tetrahydro-2H-pyran-3,4,5-triol

Base Information

• Chemical Name: (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(isopropylthio)tetrahydro-2H-pyran-3,4,5-triol
• CAS No.: 19165-11-8
• Molecular Formula: C9H18 O5 S
• Molecular Weight: 238.3
• Hs Code.: 2938909090
• European Community (EC) Number: 633-782-2
• Nikkaji Number: J732.698J
• Mol file: 19165-11-8.mol

Synonyms:19165-11-8;Isopropyl beta-D-thioglucopyranoside;(2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(isopropylthio)tetrahydro-2H-pyran-3,4,5-triol;Isopropyl |A-D-thioglucopyranoside;isopropyl-beta-d-thioglucopyranoside;(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-propan-2-ylsulfanyloxane-3,4,5-triol;Isopropyl 1-thio-beta-D-glucopyranoside;beta-D-Glucopyranoside, 1-methylethyl 1-thio-;(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(propan-2-ylsulfanyl)oxane-3,4,5-triol;SCHEMBL1032089;isopropyl B-D-thioglucopyranoside;CHEBI:177463;CCG-50219;Isopropyl beta -D-thioglucopyranoside;HY-W145651;CS-0226080;SR-01000639614-1;(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-propan-2-ylsulanyloxane-3,4,5-triol

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

Chemical Property:

• Vapor Pressure: 1.58E-09mmHg at 25°C
• Refractive Index: 1.577
• Boiling Point: 438.4°C at 760 mmHg
• PKA: 13.00±0.70(Predicted)
• Flash Point: 219°C
• PSA: 115.45000
• Density: 1.37g/cm³
• LogP: -1.07210
• Storage Temp.: −20°C
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 238.08749484
• Heavy Atom Count: 15
• Complexity: 201

Purity/Quality:

98%Min ^*data from raw suppliers

Isopropyl β-D-thioglucopyranoside ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 45-46-20/21/22-36/37/38
• Safety Statements: 53-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)SC1C(C(C(C(O1)CO)O)O)O
• Isomeric SMILES: CC(C)S[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O

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

There total 5 articles about (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(isopropylthio)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: 84.0%

isopropyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (55692-84-7) → isopropyl 1-thio-β-D-glucopyranoside (19165-11-8)

Guidance literature:

With sodium methylate; In methanol; for 0.5h;

Reference yield:

D-Glucose (2280-44-6) → isopropyl 1-thio-β-D-glucopyranoside (19165-11-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaOAc / 0.17 h / Heating

1.2: BF₃*Et₂O / CH₂Cl₂; diethyl ether / 1 h / 20 °C

2.1: 23.4 g / NaOMe / methanol / 5 h / 20 °C / pH 10

With sodium methylate; sodium acetate; In methanol;

DOI:10.1016/S0008-6215(03)00381-1

Reference yield:

2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4,6207-76-7,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,10343-06-3) → isopropyl 1-thio-β-D-glucopyranoside (19165-11-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / NaH / CH₂Cl₂ / 0.33 h / Ambient temperature

2: 92 percent / 0.1 M BF₃*OEt₂, Molekularsieb 4 A / CH₂Cl₂ / 2 h / Ambient temperature

3: 84 percent / 0.5 M CH₃ONa / methanol / 0.5 h

With Molekularsieb 4 A; boron trifluoride diethyl etherate; sodium methylate; sodium hydride; In methanol; dichloromethane;

upstream raw materials:

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

D-Glucose

2,3,4,5-tetra-O-acetyl-D-glucopyranose

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate

Downstream raw materials:

C₂₅H₃₄O₇S

C₄₉H₆₉NO₉

allyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-4,6-di-O-benzoyl-α-D-mannopyranoside

1-isopropyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside

Refernces

• 1、 Cai, Lei,Fang, Jing,Li, Ting,Song, Zejin,Sun, Jiuchang,Wan, Qian,Xiao, Xiong,Zeng, Jing. "One-Pot Relay Glycosylation". supporting information. p. 5498 - 5503. Retrieved 2020/04/09.
• 2、 Schmidt, Richard R.,Stumpp, Michael. "Glycosylimidates, 8. - Synthesis of 1-Thioglycosides". . p. 1249 - 1256. Retrieved 2007/10/02.