2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate
• CAS No.: 113893-72-4
• Molecular Formula: C₁₄H₁₈Cl₃NO₈
• Molecular Weight: 434.658
• Mol file: 113893-72-4.mol

Synonyms:2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate

Chemical Property of 2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate

There total 1 articles about 2,3,4-tri-O-acetyl-L-rhamnopyranosyl 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: 65.0%

methyl 1-O-allyl-3,4-di-O-methoxymethyl-β-D-glucuronate (616861-49-5) + 2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl trichloroacetimidate (616861-60-0) → 2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate (113893-72-4) + methyl (2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)-(allyl 3,4-di-O-methoxymethyl-β-D-glucopyranosid)uronate (616861-51-9)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 2h;

DOI:10.1016/S0008-6215(03)00195-2

Reference yield: 99.0%

methyl 6-O-[tert-butyl(diphenyl)silyl]-2,3-di-O-methyl-α-D-glucopyranoside (938081-97-1) + 2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate (113893-72-4) → methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->4)-6-O-[tert-butyl(diphenyl)silyl]-2,3-di-O-methyl-α-D-glucopyranoside (938082-00-9)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/ol070496q

Reference yield: 98.6%

(2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol (103348-50-1) + 2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate (113893-72-4) → (2S,3R,4E)-2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyl-(1'->1)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol (914803-33-1)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at -20 ℃;

DOI:10.1080/07328300600859825

upstream raw materials:

methyl 1-O-allyl-3,4-di-O-methoxymethyl-β-D-glucuronate

2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl trichloroacetimidate

Downstream raw materials:

dibenzyl 2,3,4-tri-O-acetyl-6-deoxy-α-L-talopyranosyl phosphate

2,3,4-tri-O-acetyl-6-deoxy-α-L-talopyranosyl diphenylphosphinate

Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-2-[(2S,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-6-methyl-tetrahydro-pyran-4-yloxy]-6-methyl-tetrahydro-pyran-3-yl ester

Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-6-methyl-2-[(2R,3aR,4S,6S,7R,7aR)-4-methyl-6-(4-nitro-phenoxy)-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy]-tetrahydro-pyran-3-yl ester

Refernces