(2R,3R,4R,5S,6R)-2-(acetoxymethyl)-6-phenyltetrahydro-2H-pyran-3,4,5-triyltriacetate

Base Information

• Chemical Name: (2R,3R,4R,5S,6R)-2-(acetoxymethyl)-6-phenyltetrahydro-2H-pyran-3,4,5-triyltriacetate
• CAS No.: 99212-20-1
• Molecular Formula: C₂₀H₂₄O₉
• Molecular Weight: 408.405
• Mol file: 99212-20-1.mol

Synonyms:(2R,3R,4R,5S,6R)-2-(acetoxymethyl)-6-phenyltetrahydro-2H-pyran-3,4,5-triyltriacetate

Chemical Property of (2R,3R,4R,5S,6R)-2-(acetoxymethyl)-6-phenyltetrahydro-2H-pyran-3,4,5-triyltriacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5S,6R)-2-(acetoxymethyl)-6-phenyltetrahydro-2H-pyran-3,4,5-triyltriacetate

There total 44 articles about (2R,3R,4R,5S,6R)-2-(acetoxymethyl)-6-phenyltetrahydro-2H-pyran-3,4,5-triyltriacetate 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: 85.0%

acetic anhydride (108-24-7) + C-[4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl]benzene (125412-60-4) → (2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-phenyltetrahydro-2H-pyran-3,4,5-triyl triacetate (3682-06-2,13231-13-5,15356-52-2,99212-20-1,138284-52-3,138284-53-4)

Guidance literature:

C-[4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl]benzene; With 4-methylmorpholine N-oxide; osmium(VIII) oxide; In water; acetone; at 20 ℃; for 24h;

acetic anhydride; With pyridine; dmap; at 20 ℃; Further stages.;

DOI:10.1016/j.tetlet.2004.05.046

Reference yield: 84.0%

iodobenzene (591-50-4) + acetobromomannose (13242-53-0) → (2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-phenyltetrahydro-2H-pyran-3,4,5-triyl triacetate (3682-06-2,13231-13-5,15356-52-2,99212-20-1,138284-52-3,138284-53-4)

Guidance literature:

With dmap; nickel(II) perchlorate hexahydrate; hydrogen bromide; acetic acid; magnesium chloride; zinc; In tetrahydrofuran; at 0 ℃; for 12h; stereoselective reaction; Schlenk technique; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.orglett.8b03567

Reference yield: 80.0%

phenylzinc iodide-lithium chloride complex + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → D-glucal triacetate (2873-29-2) + (2R,3R,4R,5S,6R)-2-(acetoxymethyl)-6-phenyltetrahydro-2H-pyran-3,4,5-triyltriacetate (99212-20-1)

Guidance literature:

With bis (1,5-cyclopentadiene)nickel ⁽⁰⁾; 2,6-bis(4,5-dihydrooxazol-2-yl)pyridine; In N,N-dimethyl-formamide; at 25 ℃; for 12h; optical yield given as %de;

DOI:10.1021/ja8041564

upstream raw materials:

diethyl ether

acetobromomannose

diphenyl cadmium

phenyllithium

Downstream raw materials:

(2R,3S,4R,4aS,10aR)-6,6,8,8-Tetraisopropyl-2-phenyl-hexahydro-1,5,7,9-tetraoxa-6,8-disila-benzocyclooctene-3,4-diol

(2S,3S,4R,4aS,10aR)-6,6,8,8-Tetraisopropyl-2-phenyl-hexahydro-1,5,7,9-tetraoxa-6,8-disila-benzocyclooctene-3,4-diol

(2R,4aR,6R,7R,8R,8aS)-2,6-Diphenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

α-1,5-anhydro-2,3,4,6-tetra-O-methyl-1-C-phenyl-D-glucitol

Refernces

• 1、 Mou, Ze-Dong,Wang, Jia-Xi,Zhang, Xia,Niu, Dawen. "Stereoselective Preparation of C-Aryl Glycosides via Visible-Light-Induced Nickel-Catalyzed Reductive Cross-Coupling of Glycosyl Chlorides and Aryl Bromides". supporting information. p. 3025 - 3029. Retrieved 2021/05/27.
• 2、 Adak, Laksmikanta,Kawamura, Shintaro,Toma, Gabriel,Takenaka, Toshio,Isozaki, Katsuhiro,Takaya, Hikaru,Orita, Akihiro,Li, Ho C.,Shing, Tony K. M.,Nakamura, Masaharu. "Synthesis of Aryl C-Glycosides via Iron-Catalyzed Cross Coupling of Halosugars: Stereoselective Anomeric Arylation of Glycosyl Radicals". supporting information. p. 10693 - 10701. Retrieved 2017/08/15.