p-iodophenyl (3-O-allyl-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-(4-O-benzyl-2-O-methyl)-α-L-rhamnopyranoside

Base Information

• Chemical Name: p-iodophenyl (3-O-allyl-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-(4-O-benzyl-2-O-methyl)-α-L-rhamnopyranoside
• CAS No.: 1425471-76-6
• Molecular Formula: C₄₃H₄₇IO₁₀
• Molecular Weight: 850.745

Synonyms:p-iodophenyl (3-O-allyl-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-(4-O-benzyl-2-O-methyl)-α-L-rhamnopyranoside

Chemical Property of p-iodophenyl (3-O-allyl-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-(4-O-benzyl-2-O-methyl)-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-iodophenyl (3-O-allyl-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-(4-O-benzyl-2-O-methyl)-α-L-rhamnopyranoside

There total 9 articles about p-iodophenyl (3-O-allyl-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-(4-O-benzyl-2-O-methyl)-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: 83.0%

p-iodophenyl 2-O-methyl-4-O-benzyl-α-L-rhamnopyranoside (1425471-60-8) + C30H32O5S → p-iodophenyl (3-O-allyl-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-(4-O-benzyl-2-O-methyl)-α-L-rhamnopyranoside (1425471-76-6)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -25 - 20 ℃; for 0.75h; Molecular sieve;

DOI:10.1016/j.ejmech.2017.03.058

Reference yield: 71.0%

p-iodophenyl 2-O-methyl-4-O-benzyl-α-L-rhamnopyranoside (1425471-60-8) + phenyl 2-O-benzoyl-3-O-allyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside (1425471-68-6) → p-iodophenyl (3-O-allyl-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-(4-O-benzyl-2-O-methyl)-α-L-rhamnopyranoside (1425471-76-6)

Guidance literature:

p-iodophenyl 2-O-methyl-4-O-benzyl-α-L-rhamnopyranoside; phenyl 2-O-benzoyl-3-O-allyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside; With N-(phenylthio)-ε-caprolactam; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; toluene; at 20 ℃; for 0.333333h;

With trifluoromethylsulfonic anhydride; In dichloromethane; toluene; at -25 - 20 ℃;

DOI:10.1002/anie.201206221

Reference yield:

L-rhamnose (73-34-7) → p-iodophenyl (3-O-allyl-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-(4-O-benzyl-2-O-methyl)-α-L-rhamnopyranoside (1425471-76-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: dmap / pyridine / 0 - 20 °C

2.1: boron trifluoride diethyl etherate / dichloromethane / 6 h / 20 °C

3.1: methanol; sodium / 16 h / 20 °C

4.1: (1S)-10-camphorsulfonic acid / acetone / 15 h / 20 °C

5.1: sodium hydride / N,N-dimethyl-formamide / 16 h / 20 °C

6.1: trifluoroacetic acid / tetrahydrofuran; water / 16 h / 20 °C

7.1: di(n-butyl)tin oxide; tetra-(n-butyl)ammonium iodide / toluene / 10 h / 90 °C

8.1: sodium hydride / N,N-dimethyl-formamide / 15 h / 20 °C

9.1: methanol; palladium dichloride / 15 h / 20 °C

10.1: N-(phenylthio)-ε-caprolactam; 2,4,6-tri-tert-butylpyrimidine / dichloromethane; toluene / 0.33 h / 20 °C

10.2: -25 - 20 °C

With methanol; dmap; N-(phenylthio)-ε-caprolactam; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; sodium; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; trifluoroacetic acid; palladium dichloride; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; pyridine; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1002/anie.201206221

upstream raw materials:

1,2,3,4-tetra-O-acetyl-L-rhamnopyranose

p-iodophenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranoside

L-rhamnose

p-iodophenyl 2,3-O-isopropylidene-4-O-benzyl-α-L-rhamnopyranoside

Downstream raw materials:

(3-O-allyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-p-iodophenyl 2-O-methyl-4-O-benzyl-α-L-rhamnopyranoside

(2-O-benzyl-3-O-allyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-p-iodophenyl 2-O-methyl-4-O-benzyl-α-L-rhamnopyranoside

(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-p-iodophenyl 2-O-methyl-4-O-benzyl-α-L-rhamnopyranoside

p-iodophenyl (3,4-di-O-acetyl-2-O-methyl-α-L-fucopyranosyl)-(1→3)-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-(4-O-benzyl-2-O-methyl)-α-L-rhamnopyranoside

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