1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-L-iditol

Base Information

• Chemical Name: 1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-L-iditol
• CAS No.: 881185-94-0
• Molecular Formula: C₃₆H₄₁NO₈S
• Molecular Weight: 647.789
• Mol file: 881185-94-0.mol

Synonyms:1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-L-iditol

Chemical Property of 1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-L-iditol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-L-iditol

There total 3 articles about 1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-L-iditol 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: 60.0%

Acetic acid (2S,3R,4S)-3,4-bis-benzyloxy-5-benzyloxymethyl-5-hydroxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester (881185-90-6) → 1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-D-glucitol (881185-53-1) + 1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-L-iditol (881185-94-0)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at -78 - 20 ℃;

DOI:10.1016/j.tet.2005.11.037

Reference yield:

3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-D-glucitol (881185-41-7) → 1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-L-iditol (881185-94-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 66 percent / pyridine; DMAP / 1 h / -15 °C

2: 83 percent / PDC / CH₂Cl₂ / 8 h / 45 °C

3: 60 percent / CeCl₃*7H₂O; NaBH₄ / methanol / -78 - 20 °C

With pyridine; dmap; sodium tetrahydroborate; dipyridinium dichromate; cerium(III) chloride; In methanol; dichloromethane;

DOI:10.1016/j.tet.2005.11.037

Reference yield:

1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-D-glucitol (881185-53-1) → 1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-L-iditol (881185-94-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / PDC / CH₂Cl₂ / 8 h / 45 °C

2: 60 percent / CeCl₃*7H₂O; NaBH₄ / methanol / -78 - 20 °C

With sodium tetrahydroborate; dipyridinium dichromate; cerium(III) chloride; In methanol; dichloromethane;

DOI:10.1016/j.tet.2005.11.037

upstream raw materials:

Acetic acid (2S,3R,4S)-3,4-bis-benzyloxy-5-benzyloxymethyl-5-hydroxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester

3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-D-glucitol

1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-D-glucitol

Downstream raw materials:

(2S,3R,4R,5R)-3,4-di-O-benzyl-5-benzyloxymethyl-2-hydroxymethyl-N-(p-toluenesulfonamido)pyrrolidine

5(R)-<(Benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(hydroxymethyl)pyrrolidine

(2S,3R,4R,5R)-2-acetoxymethyl-3,4-di-O-benzyl-5-benzyloxymethyl-N-(p-toluenesulfonamido)pyrrolidine