Methyl 3-O-Allyl-4,6-O-benzylidene-a-D-mannopyranoside

Base Information

• Chemical Name: Methyl 3-O-Allyl-4,6-O-benzylidene-a-D-mannopyranoside
• CAS No.: 82228-10-2
• Molecular Formula: C17H22 O6
• Molecular Weight: 322.35
• Mol file: 82228-10-2.mol

Synonyms:a-D-Mannopyranoside, methyl4,6-O-(phenylmethylene)-3-O-2-propenyl- (9CI); Pyrano[3,2-d]-1,3-dioxin, a-D-mannopyranoside deriv.

Chemical Property of Methyl 3-O-Allyl-4,6-O-benzylidene-a-D-mannopyranoside

Chemical Property:

• Vapor Pressure: 7.65E-10mmHg at 25°C
• Refractive Index: 1.555
• Boiling Point: 475.3°C at 760 mmHg
• Flash Point: 241.3°C
• PSA: 66.38000
• Density: 1.23g/cm³
• LogP: 1.40400
• Solubility.: Chloroform, Ethyl Acetate

Purity/Quality:

98% ^*data from raw suppliers

Methyl3-O-Allyl-4,6-O-benzylidene-α-D-mannopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl 3-O-Allyl-4,6-O-benzylidene-a-D-mannopyranoside is a useful synthetic intermediate.

Technology Process of Methyl 3-O-Allyl-4,6-O-benzylidene-a-D-mannopyranoside

There total 4 articles about Methyl 3-O-Allyl-4,6-O-benzylidene-a-D-mannopyranoside 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: 94.0%

(4aR,6S,7S,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (4148-58-7) + allyl bromide (106-95-6) → methyl 3-O-allyl-4,6-O-benzylidene-α-D-mannopyranoside (82228-10-2)

Guidance literature:

With iron(III) tris(2,2,6,6-tetramethyl-3,5-heptanedionate); tetrabutylammomium bromide; silver(l) oxide; In acetonitrile; at 40 ℃; for 2h; regioselective reaction;

DOI:10.1039/c7ra10220h

Reference yield:

(4aR,6S,7S,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (4148-58-7) + allyl iodid (556-56-9) → methyl 2-O-allyl-4,6-O-benzylidene-α-D-mannopyranoside (82228-09-9) + methyl 3-O-allyl-4,6-O-benzylidene-α-D-mannopyranoside (82228-10-2)

Guidance literature:

With ammonium hydroxide; water; sodium hydride; copper dichloride; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) tetrahydrofuran; reflux, 24 h., 2.) cool, tetrahydrofuran;

DOI:10.1016/S0008-6215(00)81068-X

Reference yield:

allyl iodid (556-56-9) + (4aS,6R,7S,8R,8aR)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (3162-96-7,4148-58-7,4153-17-7,4288-93-1,5328-47-2,6988-39-2,13566-32-0,14155-23-8,27994-50-9,37093-57-5,37093-59-7,57701-27-6,59168-66-0,64552-06-3,65391-13-1,65391-14-2,65530-26-9,66512-65-0,71117-36-7,71117-37-8,71117-41-4,72904-85-9,74560-56-8,79549-74-9,86783-81-5,96093-51-5,98633-13-7,110415-35-5,110415-36-6,110850-29-8,124020-29-7,126924-12-7,129263-21-4,131433-03-9,145920-49-6,146863-04-9) → methyl 2-O-allyl-4,6-O-benzylidene-α-D-allopyranoside (20770-92-7,81600-89-7,82228-07-7,82228-09-9,93221-22-8,95188-91-3,109010-82-4,131614-84-1) + (4aS,6R,7S,8R,8aS)-8-Allyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (20770-87-0,65877-24-9,82228-08-8,82228-10-2,93221-23-9,109010-83-5,131614-87-4,141318-01-6)

Guidance literature:

With di(n-butyl)tin oxide; Yield given. Multistep reaction. Yields of byproduct given; 1.) methanol, reflux, 90 min; 2.) DMF, 1 h, 100 deg C;

DOI:10.1016/S0040-4020(01)87284-7

upstream raw materials:

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

allyl iodid

allyl bromide

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

Downstream raw materials:

8-methoxycarbonyloctyl-6-O-acetyl-3-O-allyl-2,4-di-O-benzyl-α-D-mannopyranosyl bromide

8-methoxycarbonyloctyl-6-O-acetyl-3-O-allyl-2,4-di-O-benzyl-β-D-mannopyranosyl bromide

methyl 6-O-acetyl-3-O-allyl-2,4-di-O-benzyl-α-D-mannopyranoside

methyl 3-O-allyl-2,6-di-O-benzyl-α-D-mannopyranoside

Refernces

• 1、 Vatele, J.-M.. "SYNTHETIC STUDIES ON NOGALAMYCIN: STEREOSPECIFIC C-5 ALKYLATION OF A SUGAR DERIVATIVE VIA CLAISEN REARRANGEMENT AND A NEW ROUTE TO 1,1,4-TRIALKOXYBUTA-1,3-DIENES.". . p. 4443 - 4450. Retrieved 2007/10/02.