p-nitrophenyl 2-O-acetyl-4-O-benzyl-3-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside

Base Information

• Chemical Name: p-nitrophenyl 2-O-acetyl-4-O-benzyl-3-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside
• CAS No.: 86795-40-6
• Molecular Formula: C₄₈H₅₁NO₁₂
• Molecular Weight: 833.932
• Mol file: 86795-40-6.mol

Synonyms:p-nitrophenyl 2-O-acetyl-4-O-benzyl-3-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside

Chemical Property of p-nitrophenyl 2-O-acetyl-4-O-benzyl-3-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrophenyl 2-O-acetyl-4-O-benzyl-3-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside

There total 5 articles about p-nitrophenyl 2-O-acetyl-4-O-benzyl-3-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside 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: 72.0%

(2S,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-chloro-6-methyltetrahydro-2H-pyran (86795-39-3) + p-nitrophenyl 2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside (86795-37-1) → p-nitrophenyl 2-O-acetyl-4-O-benzyl-3-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside (86795-40-6)

Guidance literature:

With 2,4,6-trimethyl-pyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; -40 deg C -> r.t.;

DOI:10.1016/0008-6215(83)88121-X

Reference yield:

benzyl bromide (100-39-0) → p-nitrophenyl 2-O-acetyl-4-O-benzyl-3-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside (86795-40-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) p-toluenesulfonic acid monohydrate; 2.) sodium hydride / 1.) toluene, r.t., 1 h; 2.) N,N-dimethylformamide; 3.) 3 h

2: 80 percent acetic acid / H₂O / 1 h / Ambient temperature

3: 72 percent / silver triflate, 2,4,6-trimethylpyridine, 4 Angstroem molecular sieves / CH₂Cl₂ / -40 deg C -> r.t.

With 2,4,6-trimethyl-pyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; sodium hydride; toluene-4-sulfonic acid; acetic acid; In dichloromethane; water;

DOI:10.1016/0008-6215(83)88121-X

Reference yield:

(3aR,4S,6S,7S,7aR)-7-Benzyloxy-2,6-dimethyl-4-(4-nitro-phenoxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-ol → p-nitrophenyl 2-O-acetyl-4-O-benzyl-3-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside (86795-40-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent acetic acid / H₂O / 1 h / Ambient temperature

2: 72 percent / silver triflate, 2,4,6-trimethylpyridine, 4 Angstroem molecular sieves / CH₂Cl₂ / -40 deg C -> r.t.

With 2,4,6-trimethyl-pyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; acetic acid; In dichloromethane; water;

DOI:10.1016/0008-6215(83)88121-X

upstream raw materials:

(2S,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-chloro-6-methyltetrahydro-2H-pyran

p-nitrophenyl 2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

benzyl bromide

2,3,4-tri-O-(phenylmethyl)-α-L-rhamnopyranoside

Downstream raw materials:

p-aminophenyl 2-O-acetyl-3-O-α-L-rhamnopyranosyl-α-L-rhamnopyranoside