Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[(2R,4aR,8R,8aS)-2-(4-methoxy-phenyl)-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[(2R,4aR,8R,8aS)-2-(4-methoxy-phenyl)-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-tetrahydro-pyran-3-yl ester
• CAS No.: 196704-63-9
• Molecular Formula: C₄₃H₄₆O₁₁
• Molecular Weight: 738.832
• Mol file: 196704-63-9.mol

Synonyms:Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[(2R,4aR,8R,8aS)-2-(4-methoxy-phenyl)-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[(2R,4aR,8R,8aS)-2-(4-methoxy-phenyl)-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[(2R,4aR,8R,8aS)-2-(4-methoxy-phenyl)-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-tetrahydro-pyran-3-yl ester

There total 1 articles about Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[(2R,4aR,8R,8aS)-2-(4-methoxy-phenyl)-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-tetrahydro-pyran-3-yl ester 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: 67.0%

ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside (142819-21-4) + 2,6-anhydro-5-deoxy-1,3-O-(4-methoxybenzylidene)-D-arabino-hex-5-enitol (187880-20-2) → (2R,4aR,8R,8aS)-8-((3aR,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-2-yloxy)-2-(4-methoxy-phenyl)-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine + Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[(2R,4aR,8R,8aS)-2-(4-methoxy-phenyl)-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-tetrahydro-pyran-3-yl ester (196704-63-9)

Guidance literature:

With 4 A molecular sieve; Di-tert-butylpyridine; methyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 15h;

DOI:10.1021/ja971640d

Reference yield:

Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[(2R,4aR,8R,8aS)-2-(4-methoxy-phenyl)-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-tetrahydro-pyran-3-yl ester (196704-63-9) → Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[(1aS,2aR,5R,6aR,7S,7aR)-5-(4-methoxy-phenyl)-hexahydro-1,2,4,6-tetraoxa-cyclopropa[b]naphthalen-7-yloxy]-tetrahydro-pyran-3-yl ester

Guidance literature:

With 3,3-dimethyldioxirane; In dichloromethane; acetone;

DOI:10.1021/ja971640d

Reference yield:

Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[(2R,4aR,8R,8aS)-2-(4-methoxy-phenyl)-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-tetrahydro-pyran-3-yl ester (196704-63-9) → C59H64O18

Guidance literature:

Multi-step reaction with 4 steps

1: dimethyldioxirane / acetone; CH₂Cl₂

2: trifluoroacetic acid anhydride / CH₂Cl₂

3: 100 percent / DMAP; pyridine

4: 81 percent / methyl triflate; di-tert-butylpyridine; 4 Angstroem molecular sieves

With pyridine; dmap; 4 A molecular sieve; 3,3-dimethyldioxirane; Di-tert-butylpyridine; trifluoroacetic anhydride; methyl trifluoromethanesulfonate; In dichloromethane; acetone; 1: Epoxidation / 2: Ring cleavage / 3: Acetylation / 4: Cyclization;

DOI:10.1021/ja971640d

upstream raw materials:

ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

2,6-anhydro-5-deoxy-1,3-O-(4-methoxybenzylidene)-D-arabino-hex-5-enitol

Downstream raw materials:

thioethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->3)-4,6-O-(4-methoxy)benzylidene-β-D-glucopyranoside

Acetic acid (2R,4aR,6S,7R,8S,8aR)-8-((2S,3R,4S,5R,6R)-3-acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-6-ethylsulfanyl-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

thioethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->3)-4,6-O-(4-methoxy)benzylidene-2-O-pivaloyl-β-D-glucopyranoside

Benzoic acid (2R,4aR,6S,7R,8S,8aR)-8-((2S,3R,4S,5R,6R)-3-acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-6-ethylsulfanyl-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester