2,4,6-tri-O-acetyl-3-O-benzyl-L-idopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 2,4,6-tri-O-acetyl-3-O-benzyl-L-idopyranosyl trichloroacetimidate
• CAS No.: 256348-52-4
• Molecular Formula: C₂₁H₂₄Cl₃NO₉
• Molecular Weight: 540.782
• Mol file: 256348-52-4.mol

Synonyms:2,4,6-tri-O-acetyl-3-O-benzyl-L-idopyranosyl trichloroacetimidate

Chemical Property of 2,4,6-tri-O-acetyl-3-O-benzyl-L-idopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,4,6-tri-O-acetyl-3-O-benzyl-L-idopyranosyl trichloroacetimidate

There total 2 articles about 2,4,6-tri-O-acetyl-3-O-benzyl-L-idopyranosyl trichloroacetimidate 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:

1,2,4,6-tetra-O-acetyl-3-O-benzyl-L-idopyranoside (118711-49-2) → 2,4,6-tri-O-acetyl-3-O-benzyl-L-idopyranosyl trichloroacetimidate (256348-52-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 61 percent / piperidine / acetic acid; tetrahydrofuran

2: Cs₂CO₃ / CH₂Cl₂

With piperidine; caesium carbonate; In tetrahydrofuran; dichloromethane; acetic acid; 1: Deacetylation / 2: Addition;

DOI:10.1016/S0040-4039(99)01084-9

Reference yield:

trichloroacetonitrile (545-06-2) + Acetic acid (2S,3R,4S,5R)-5-acetoxy-2-acetoxymethyl-4-benzyloxy-6-hydroxy-tetrahydro-pyran-3-yl ester → 2,4,6-tri-O-acetyl-3-O-benzyl-L-idopyranosyl trichloroacetimidate (256348-52-4)

Guidance literature:

With caesium carbonate; In dichloromethane;

DOI:10.1016/S0040-4039(99)01084-9

Reference yield: 83.0%

methyl N-benzyloxycarbonyl-2-deoxy-3,6-di-O-benzylglucopyranoside (110236-56-1) + 2,4,6-tri-O-acetyl-3-O-benzyl-L-idopyranosyl trichloroacetimidate (256348-52-4) → Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester (110236-57-2)

Guidance literature:

With tin(II) trifluoromethanesulfonate; In dichloromethane; at 0 ℃;

DOI:10.1016/S0960-894X(99)00550-8

upstream raw materials:

trichloroacetonitrile

1,2,4,6-tetra-O-acetyl-3-O-benzyl-L-idopyranoside

Downstream raw materials:

methyl 2,4,6-tri-O-acetyl-3-O-benzyl-α-L-idopyranoside

Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester

Acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-3-((2S,3R,4S,5R,6S)-3,5-diacetoxy-6-acetoxymethyl-4-benzyloxy-tetrahydro-pyran-2-yloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Acetic acid (2R,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-((2R,3R,4S,5R,6R)-3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester