methyl 2,3,6-tri-O-benzyl-4-deoxy-4-(iodomethyl)-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2,3,6-tri-O-benzyl-4-deoxy-4-(iodomethyl)-α-D-glucopyranoside
• CAS No.: 138459-11-7
• Molecular Formula: C₂₉H₃₃IO₅
• Molecular Weight: 588.483
• Mol file: 138459-11-7.mol

Synonyms:methyl 2,3,6-tri-O-benzyl-4-deoxy-4-(iodomethyl)-α-D-glucopyranoside

Chemical Property of methyl 2,3,6-tri-O-benzyl-4-deoxy-4-(iodomethyl)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3,6-tri-O-benzyl-4-deoxy-4-(iodomethyl)-α-D-glucopyranoside

There total 9 articles about methyl 2,3,6-tri-O-benzyl-4-deoxy-4-(iodomethyl)-α-D-glucopyranoside 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%

METHYL 2,3,6-TRI-O-BENZYL-4-DEOXY-4-HYDROXYMETHYL-α-D-GLUCO-PYRANOSIDE (127243-54-3) → methyl 2,3,6-tri-O-benzyl-4-deoxy-4-(iodomethyl)-α-D-glucopyranoside (138459-11-7)

Guidance literature:

With N-iodo-succinimide; triphenylphosphine; In N,N-dimethyl-formamide; at 50 ℃; for 2h;

DOI:10.1021/jo00029a024

Reference yield:

methyl 2,3,6-Tri-O-Benzyl-4-Deoxy-4-Formyl-α-D-Gluco-Pyranoside (127214-51-1) → methyl 2,3,6-tri-O-benzyl-4-deoxy-4-(iodomethyl)-α-D-glucopyranoside (138459-11-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / NaBH₄ / methanol / 4 h / 0 °C

2: 4-dimethylaminopyridine; pyridine / 48 h / 20 °C

3: 283 mg / NaI / acetone / 5 h / 70 °C

With pyridine; dmap; sodium tetrahydroborate; sodium iodide; In methanol; acetone;

DOI:10.1021/ol030081e

Reference yield:

Toluene-4-sulfonic acid (2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl ester → methyl 2,3,6-tri-O-benzyl-4-deoxy-4-(iodomethyl)-α-D-glucopyranoside (138459-11-7)

Guidance literature:

With sodium iodide; In acetone; at 70 ℃; for 5h;

DOI:10.1021/ol030081e

upstream raw materials:

METHYL 2,3,6-TRI-O-BENZYL-4-DEOXY-4-HYDROXYMETHYL-α-D-GLUCO-PYRANOSIDE

methyl 2,3,6-Tri-O-Benzyl-4-Deoxy-4-Formyl-α-D-Gluco-Pyranoside

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

1-O-methyl-2,3,6-tri-O-benzyl-4-keto-α-D-glucopyranoside

Downstream raw materials:

Methyl 2,3,6-Tri-O-benzyl-4-deoxy-4-C-(3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-2-heptulopyranos-1-yl)-α-D-glucopyranoside

Methyl 4-deoxy-4-C-(triphenylmethylenephosphonium iodide)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

Methyl 4-deoxy-2,3,6-tri-O-benzyl-4-C-(2-bromo-1,2-dideoxy-3,4-O-isopropylidene-β-D-gluco-hexopyranos-1-yl)-α-D-gluco-hexopyranoside

Methyl 4-deoxy-2,3,6-tri-O-benzyl-4-C-(2-bromo-6-O-(tert-butyldiphenylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-β-D-gluco-hexopyranos-1-yl)-α-D-gluco-hexopyranoside