1,3,4-O-triacetoxy-5-deoxy-6-O-[5'-deoxy-2',3',4',6'-O-tetrakis(4-methoxyphenylmethyl)-5'-thio-α-D-glucopyranosyl]-2-O-methoxymethyl-5-thio-β-D-glucopyranose

Base Information

• Chemical Name: 1,3,4-O-triacetoxy-5-deoxy-6-O-[5'-deoxy-2',3',4',6'-O-tetrakis(4-methoxyphenylmethyl)-5'-thio-α-D-glucopyranosyl]-2-O-methoxymethyl-5-thio-β-D-glucopyranose
• CAS No.: 756485-49-1
• Molecular Formula: C₅₂H₆₄O₁₇S₂
• Molecular Weight: 1025.2

Synonyms:1,3,4-O-triacetoxy-5-deoxy-6-O-[5'-deoxy-2',3',4',6'-O-tetrakis(4-methoxyphenylmethyl)-5'-thio-α-D-glucopyranosyl]-2-O-methoxymethyl-5-thio-β-D-glucopyranose

Chemical Property of 1,3,4-O-triacetoxy-5-deoxy-6-O-[5'-deoxy-2',3',4',6'-O-tetrakis(4-methoxyphenylmethyl)-5'-thio-α-D-glucopyranosyl]-2-O-methoxymethyl-5-thio-β-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,3,4-O-triacetoxy-5-deoxy-6-O-[5'-deoxy-2',3',4',6'-O-tetrakis(4-methoxyphenylmethyl)-5'-thio-α-D-glucopyranosyl]-2-O-methoxymethyl-5-thio-β-D-glucopyranose

There total 9 articles about 1,3,4-O-triacetoxy-5-deoxy-6-O-[5'-deoxy-2',3',4',6'-O-tetrakis(4-methoxyphenylmethyl)-5'-thio-α-D-glucopyranosyl]-2-O-methoxymethyl-5-thio-β-D-glucopyranose 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:

acetic anhydride (108-24-7) + 5-deoxy-6-O-[5'-deoxy-2',3',4',6'-O-tetrakis(4-methoxyphenylmethyl)-5'-thio-α-D-glucopyranosyl]-2-O-methoxymethyl-5-thio-α-D-glucopyranose (756485-46-8) → 1,3,4-O-triacetoxy-5-deoxy-6-O-[5'-deoxy-2',3',4',6'-O-tetrakis(4-methoxyphenylmethyl)-5'-thio-α-D-glucopyranosyl]-2-O-methoxymethyl-5-thio-α-D-glucopyranose (756485-48-0) + 1,3,4-O-triacetoxy-5-deoxy-6-O-[5'-deoxy-2',3',4',6'-O-tetrakis(4-methoxyphenylmethyl)-5'-thio-α-D-glucopyranosyl]-2-O-methoxymethyl-5-thio-β-D-glucopyranose (756485-49-1)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 33h; Title compound not separated from byproducts.;

DOI:10.1016/j.tet.2004.06.006

Reference yield:

acetic anhydride (108-24-7) + 5-deoxy-6-O-[5'-deoxy-2',3',4',6'-O-tetrakis(4-methoxyphenylmethyl)-5'-thio-α-D-glucopyranosyl]-2-O-methoxymethyl-5-thio-β-D-glucopyranose (756485-47-9) → 1,3,4-O-triacetoxy-5-deoxy-6-O-[5'-deoxy-2',3',4',6'-O-tetrakis(4-methoxyphenylmethyl)-5'-thio-α-D-glucopyranosyl]-2-O-methoxymethyl-5-thio-α-D-glucopyranose (756485-48-0) + 1,3,4-O-triacetoxy-5-deoxy-6-O-[5'-deoxy-2',3',4',6'-O-tetrakis(4-methoxyphenylmethyl)-5'-thio-α-D-glucopyranosyl]-2-O-methoxymethyl-5-thio-β-D-glucopyranose (756485-49-1)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; Title compound not separated from byproducts.;

DOI:10.1016/j.tet.2004.06.006

Reference yield:

6-O-benzoyl-1,5-dideoxy-3,4-O-isopropylidene-5-thio-D-glucopyranose (592517-48-1) → 1,3,4-O-triacetoxy-5-deoxy-6-O-[5'-deoxy-2',3',4',6'-O-tetrakis(4-methoxyphenylmethyl)-5'-thio-α-D-glucopyranosyl]-2-O-methoxymethyl-5-thio-β-D-glucopyranose (756485-49-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 86 percent / i-Pr₂NEt / CH₂Cl₂ / 3 h / 20 °C

2: 43 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / -20 °C

3: 100 percent / NaOMe / methanol / 20 h / 20 °C

4: 93 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂ / 2 h / -78 - 20 °C

5: 51 percent / pyridine; trifluoroacetic anhydride / CH₂Cl₂ / 0 °C

6: 61 percent / aq. HCl / methanol / 1 h / 20 °C

7: pyridine / CH₂Cl₂ / 33 h / 20 °C

With pyridine; hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; In methanol; dichloromethane; 5: Pummerer rearrangement;

DOI:10.1016/j.tet.2004.06.006

upstream raw materials:

acetic anhydride

5-deoxy-6-O-[5'-deoxy-2',3',4',6'-O-tetrakis(4-methoxyphenylmethyl)-5'-thio-α-D-glucopyranosyl]-2-O-methoxymethyl-5-thio-α-D-glucopyranose

5-deoxy-6-O-[5'-deoxy-2',3',4',6'-O-tetrakis(4-methoxyphenylmethyl)-5'-thio-α-D-glucopyranosyl]-2-O-methoxymethyl-5-thio-β-D-glucopyranose

2,3,4,6-[tetrakis-O-(4-methoxyphenyl)methyl]-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate

Downstream raw materials:

Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-5-methoxymethoxy-6-(2,2,2-trichloro-acetimidoyloxy)-2-[(2S,3R,4S,5S,6R)-3,4,5-tris-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-thiopyran-2-yloxymethyl]-tetrahydro-thiopyran-3-yl ester

3,4-O-diacetoxy-5-deoxy-6-O-[5'-deoxy-2',3',4',6'-O-tetrakis(4-methoxyphenylmethyl)-5'-thio-α-D-glucopyranosyl]-2-O-methoxymethyl-5-thio-α-D-glucopyranose

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