3,4,6-Tri-O-benzyl-beta-D-mannopyranose-1,2-(methyl orthoacetate)

Base Information

• Chemical Name: 3,4,6-Tri-O-benzyl-beta-D-mannopyranose-1,2-(methyl orthoacetate)
• CAS No.: 16697-49-7
• Molecular Formula: C30H34O7
• Molecular Weight: 506.596
• Mol file: 16697-49-7.mol

Synonyms:3,4,6-Tri-O-benzyl--D-mannopyranose 1,2-(Methyl Orthoacetate);

Chemical Property of 3,4,6-Tri-O-benzyl-beta-D-mannopyranose-1,2-(methyl orthoacetate)

Chemical Property:

• Appearance/Colour: White Solid
• Melting Point: 74-76 °C
• Refractive Index: 1.593
• Boiling Point: 601.108 °C at 760 mmHg
• Flash Point: 232.122 °C
• PSA: 64.61000
• Density: 1.228 g/cm³
• LogP: 4.83440
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

3,4,6-Tri-O-benzyl-β-D-mannopyranose1,2-(MethylOrthoacetate) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: 3,4,6-Tri-O-benzyl-β-D-mannopyranose 1,2-(methyl orthoacetate) is a synthetic intermediate used in glycosylation reactions. Typically, the methyl orthoester protecting group is first removed by mild acid hydrolysis, producing a glycosyl donor. Removal of the O-benzyl protecting groups is performed late in the synthesis.
• Uses: 3,4,6-Tri-O-benzyl-β-D-mannopyranose 1,2-(Methyl Orthoacetate) (cas# 16697-49-7) is a compound useful in organic synthesis.

Technology Process of 3,4,6-Tri-O-benzyl-beta-D-mannopyranose-1,2-(methyl orthoacetate)

There total 28 articles about 3,4,6-Tri-O-benzyl-beta-D-mannopyranose-1,2-(methyl orthoacetate) 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: 95.0%

benzyl bromide (100-39-0) + (3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol (29073-91-4,138196-19-7,55865-04-8) → 3,4,6-tri-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose (51532-75-3,16697-49-7,68681-00-5,68779-52-2,78418-56-1,125135-29-7,130694-47-2,130694-49-4,146864-77-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1021/jo300299p

Reference yield: 92.0%

benzyl bromide (100-39-0) + 1,2-O-(1-methoxyethylidene)-β-D-mannopyranose (29073-91-4,55865-04-8,138196-19-7) → 3,4,6-tri-O-benzyl-1,2-O-(methoxyethylidene)-β-D-mannopyranose (16697-49-7)

Guidance literature:

With sodium hydride;

Reference yield: 90.0%

3,4,6-tri-O-acetyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranose (3254-16-8,4435-05-6,19189-54-9,29748-21-8,50801-29-1,64727-26-0,64727-27-1,65338-02-5,67672-68-8,78418-55-0,80877-03-8,103002-27-3,103002-29-5,132562-62-0) + benzyl chloride (100-44-7) → 3,4,6-tri-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose (51532-75-3,16697-49-7,68681-00-5,68779-52-2,78418-56-1,125135-29-7,130694-47-2,130694-49-4,146864-77-9)

Guidance literature:

With sodium hydroxide; tert-Amyl alcohol; tetra(n-butyl)ammonium hydrogensulfate; In water; benzene; for 12h; Ambient temperature;

upstream raw materials:

3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

benzyl bromide

1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

benzyl chloride

Downstream raw materials:

6-(N-benzyloxycarbonylamino)-hexyl-2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside

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

2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranoside

2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl bromide