methyl 2-deoxy-2-iodo-4,6-O-(phenylmethylene)-α-D-mannopyranoside

Base Information

• Chemical Name: methyl 2-deoxy-2-iodo-4,6-O-(phenylmethylene)-α-D-mannopyranoside
• CAS No.: 517893-16-2
• Molecular Formula: C₁₄H₁₇IO₅
• Molecular Weight: 392.19
• Mol file: 517893-16-2.mol

Synonyms:methyl 2-deoxy-2-iodo-4,6-O-(phenylmethylene)-α-D-mannopyranoside

Chemical Property of methyl 2-deoxy-2-iodo-4,6-O-(phenylmethylene)-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of methyl 2-deoxy-2-iodo-4,6-O-(phenylmethylene)-α-D-mannopyranoside

There total 6 articles about methyl 2-deoxy-2-iodo-4,6-O-(phenylmethylene)-α-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: 90.0%

4,6-O-benzylidene-1-O-methyl-2-O-trifluoromethylsulfonate-α-D-glucopyranoside (129217-24-9) → methyl 2-deoxy-2-iodo-4,6-O-(phenylmethylene)-α-D-mannopyranoside (517893-16-2)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; In toluene; at 80 ℃; for 4h; Inert atmosphere;

DOI:10.1002/anie.201403543

Reference yield: 61.0%

methyl 2-deoxy-2-iodo-α-D-mannopyranoside (10226-88-7) + benzaldehyde dimethyl acetal (1125-88-8) → methyl 2-deoxy-2-iodo-4,6-O-(phenylmethylene)-α-D-mannopyranoside (517893-16-2)

Guidance literature:

With pyridinium p-toluenesulfonate; In N,N-dimethyl-formamide; at 40 ℃; for 1h; under 15 Torr;

DOI:10.1021/jo0206667

Reference yield:

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7) → methyl 2-deoxy-2-iodo-4,6-O-(phenylmethylene)-α-D-mannopyranoside (517893-16-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / pyridine / CH₂Cl₂ / 3 h / -30 °C

2: 83 percent / tetra-n-butylammonium iodide / toluene / 4 h / 80 °C

With pyridine; tetra-(n-butyl)ammonium iodide; In dichloromethane; toluene;

DOI:10.1016/S0957-4166(03)00288-X

upstream raw materials:

methyl 2-deoxy-2-iodo-α-D-mannopyranoside

benzaldehyde dimethyl acetal

4,6-O-benzylidene-1-O-methyl-2-O-trifluoromethylsulfonate-α-D-glucopyranoside

methyl-alpha-D-glucopyranoside

Downstream raw materials:

methyl 2-deoxy-2-iodo-3-O-ethynyldimethylsilyl-4,6-O-benzylidene-α-D-mannopyranoside

4,6-O-benzylidene-D-glucal

methyl 2,3,4-tri-O-benzyl-6-O-(4,6-O-benzylidene-3-O-triisopropylsilyl-2-deoxy-α-D-erythro-hexapyranosyl)-α-D-glucopyranoside

methyl 2,3,4-tri-O-benzyl-6-O-(4,6-O-benzylidene-3-O-triisopropylsilyl-2-deoxy-β-D-erythro-hexapyranosyl)-α-D-glucopyranoside