3-O-<2'-O-(2''-O-acetyl-3'',4''-di-O-benzyl-α-L-rhamnopyranosyl)-3',4'-di-O-benzyl-α-L-rhamnopyranosyl>-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranose

Base Information

• Chemical Name: 3-O-<2'-O-(2''-O-acetyl-3'',4''-di-O-benzyl-α-L-rhamnopyranosyl)-3',4'-di-O-benzyl-α-L-rhamnopyranosyl>-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranose
• CAS No.: 109714-41-2
• Molecular Formula: C₆₂H₆₈O₁₅
• Molecular Weight: 1053.21
• Mol file: 109714-41-2.mol

Synonyms:3-O-<2'-O-(2''-O-acetyl-3'',4''-di-O-benzyl-α-L-rhamnopyranosyl)-3',4'-di-O-benzyl-α-L-rhamnopyranosyl>-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranose

Chemical Property of 3-O-<2'-O-(2''-O-acetyl-3'',4''-di-O-benzyl-α-L-rhamnopyranosyl)-3',4'-di-O-benzyl-α-L-rhamnopyranosyl>-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-<2'-O-(2''-O-acetyl-3'',4''-di-O-benzyl-α-L-rhamnopyranosyl)-3',4'-di-O-benzyl-α-L-rhamnopyranosyl>-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranose

There total 12 articles about 3-O-<2'-O-(2''-O-acetyl-3'',4''-di-O-benzyl-α-L-rhamnopyranosyl)-3',4'-di-O-benzyl-α-L-rhamnopyranosyl>-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranose 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: 90.0%

C65H72O15 (109744-31-2) → 3-O-<2'-O-(2''-O-acetyl-3'',4''-di-O-benzyl-α-L-rhamnopyranosyl)-3',4'-di-O-benzyl-α-L-rhamnopyranosyl>-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranose (109714-41-2)

Guidance literature:

With mercury dichloride; mercury(II) oxide; In water; acetone;

Reference yield:

L-rhamnose monohydrate (6155-35-7) → 3-O-<2'-O-(2''-O-acetyl-3'',4''-di-O-benzyl-α-L-rhamnopyranosyl)-3',4'-di-O-benzyl-α-L-rhamnopyranosyl>-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranose (109714-41-2)

Guidance literature:

Multi-step reaction with 8 steps

1: trifluoromethanesulphonic acid / Heating

3: 40 percent / toluene-p-sulphonic acid / acetonitrile / 18 h / Ambient temperature

4: 64 percent / 1,1,3,3-tetramethylurea, silver trifluoromethanesulphonate, molecular sieves / CH₂Cl₂ / -78 degC then allowed to warm to room temperature, 72 h

5: 72 percent / methanolic HCl / 48 h / Ambient temperature

6: 61 percent / 1,1,3,3-tetramethylurea, silver trifluoromethanesulphonic acid, molecular sieves / CH₂Cl₂ / -78 degC then allowed to warm to room temperature, 48 h

7: tris(triphenylphosphine)rhodium(I) chloride / ethanol; H₂O / 18 h / Heating

8: 90 percent / mercury(II) oxide, mercury(II) chloride / acetone; H₂O

With hydrogenchloride; Wilkinson's catalyst; molecular sieve; trifluorormethanesulfonic acid; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; tetramethylurea; mercury dichloride; mercury(II) oxide; In ethanol; dichloromethane; water; acetone; acetonitrile;

Reference yield:

3-O-<2'-O-(2''-O-acetyl-3'',4''-di-O-benzyl-α-L-rhamnopyranosyl)-3',4'-di-O-benzyl-α-L-rhamnopyranosyl>-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl chloride (109714-42-3) + allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (120142-50-9) → allyl 3-O-(3-O-(2-O-(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (120022-51-7) + 3-O-<2'-O-(2''-O-acetyl-3'',4''-di-O-benzyl-α-L-rhamnopyranosyl)-3',4'-di-O-benzyl-α-L-rhamnopyranosyl>-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranose (109714-41-2)

Guidance literature:

With 4 A molecular sieve; silver trifluoromethanesulfonate; tetramethylurea; In dichloromethane; 1.) from -78 deg C to room temperature, 2.) room temperature, 44 h;

DOI:10.1021/jo00272a038

upstream raw materials:

3-O-<2'-O-(2''-O-acetyl-3'',4''-di-O-benzyl-α-L-rhamnopyranosyl)-3',4'-di-O-benzyl-α-L-rhamnopyranosyl>-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl chloride

allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

C₆₅H₇₂O₁₅

allyl α-L-rhamnopyranoside

Downstream raw materials:

Benzoic acid (2S,3R,4R,5S,6S)-4-[(2S,3R,4R,5S,6S)-3-((2S,3R,4R,5S,6S)-3-acetoxy-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy]-5-benzyloxy-2-bromo-6-methyl-tetrahydro-pyran-3-yl ester

3-O-<2'-O-(2''-O-acetyl-3'',4''-di-O-benzyl-α-L-rhamnopyranosyl)-3',4'-di-O-benzyl-α-L-rhamnopyranosyl>-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl chloride

Refernces

• 1、 Pinto, B. Mario,Morisette, David G.. "Synthesis of Oligosaccharides Corresponding to Biological Repeating Units of Shigella flexneri Variant Y Polysaccharide. Part 1. Overall Strategy, Synthesis of a Key Trisaccharide Intermediate, and Synthesis of a Pentasaccharide". . p. 9 - 14. Retrieved 2007/10/02.