3,4,6-tri-O-benzyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose

Base Information

• Chemical Name: 3,4,6-tri-O-benzyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose
• CAS No.: 68681-00-5
• Molecular Formula: C₃₀H₃₄O₇
• Molecular Weight: 506.596
• Mol file: 68681-00-5.mol

Synonyms:3,4,6-tri-O-benzyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose

Chemical Property of 3,4,6-tri-O-benzyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3,4,6-tri-O-benzyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose

There total 20 articles about 3,4,6-tri-O-benzyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose 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: 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;

Reference yield: 84.0%

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 bromide (100-39-0) → 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:

3,4,6-tri-O-acetyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranose; With methanol; sodium; at 20 ℃;

benzyl bromide; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; Inert atmosphere;

DOI:10.1002/chem.201100732

upstream raw materials:

3,4,6-tri-O-acetyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranose

benzyl chloride

benzyl bromide

(3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

Downstream raw materials:

methyl 2,4-di-O-benzyl-(2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranosyl-α-(1→3))-(2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranosyl-α-(1→6))-α-D-mannopyranoside

8-(Methoxycarbonyl)octyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside

1,2-di-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside

phenyl 1-deoxy-2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside