2-isopropyl-5-methylcyclohexyl-4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside

Base Information

• Chemical Name: 2-isopropyl-5-methylcyclohexyl-4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside
• CAS No.: 861928-56-5
• Molecular Formula: C₂₀H₃₂O₆
• Molecular Weight: 368.47
• Mol file: 861928-56-5.mol

Synonyms:2-isopropyl-5-methylcyclohexyl-4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside

Chemical Property of 2-isopropyl-5-methylcyclohexyl-4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-isopropyl-5-methylcyclohexyl-4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside

There total 4 articles about 2-isopropyl-5-methylcyclohexyl-4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside 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: 93.0%

(-)-menthol (2216-51-5) + D-glucal triacetate (2873-29-2) → 2-isopropyl-5-methylcyclohexyl-4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside (861928-56-5)

Guidance literature:

With zinc dibromide; In chloroform; at 72 ℃; for 0.5h; stereoselective reaction; Microwave irradiation;

DOI:10.1080/00397911.2014.909490

Reference yield:

(-)-menthol (2216-51-5) + D-glucal triacetate (2873-29-2) → 2-isopropyl-5-methylcyclohexyl-4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside (861928-56-5) + L-menthyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside (1629041-66-2)

Guidance literature:

With copper(II) bis(trifluoromethanesulfonate); In acetonitrile; at 20 ℃; for 12h; Overall yield = 83 %; stereoselective reaction; Inert atmosphere; Sealed tube; Green chemistry;

DOI:10.1055/s-0033-1341232

Reference yield:

(-)-menthol (2216-51-5) + methyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranoside (3427-20-1) → 2-isopropyl-5-methylcyclohexyl-4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside (861928-56-5)

Guidance literature:

boron trifluoride diethyl etherate; In benzene; at 80 ℃; for 1.75h;

upstream raw materials:

(-)-menthol

methyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranoside

D-glucal triacetate

3,4,6-tri-O-acetyl-2-deoxy-D-arabino-hexopyranosyl bromide

Refernces

• 1、 Gurawa, Aakanksha,Kashyap, Sudhir,Kumar, Manoj,Reddy, Thurpu Raghavender. "Copper(ii)-catalyzed stereoselective 1,2-addition: Vs. Ferrier glycosylation of "armed" and "disarmed" glycal donors". . p. 4848 - 4862. Retrieved 2020/07/13.
• 2、 Tatina, Madhu Babu,Mengxin, Xia,Peilin, Rao,Judeh, Zaher M. A.. "Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated O-, C-, N- And S-linked glycosides". supporting information. p. 1275 - 1280. Retrieved 2019/07/08.