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

Base Information

Chemical Name: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
CAS No.:756485-46-8
Molecular Formula:C₄₆H₅₈O₁₄S₂
Molecular Weight:899.09
Hs Code.:

Synonyms: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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Chemical Property of 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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Technology Process of 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

There total 4 articles about 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 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: 61.0%

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

: 756485-46-8
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

: 756485-47-9
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

Guidance literature:: With hydrogenchloride; In methanol; at 20 ℃; for 1h;
DOI:10.1016/j.tet.2004.06.006

Reference yield:

: 565462-72-8
2,3,4,6-[tetrakis-O-(4-methoxyphenyl)methyl]-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate

: 756485-46-8
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

Guidance literature:: Multi-step reaction with 3 steps

1: 93 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂ / 2 h / -78 - 20 °C

2: 51 percent / pyridine; trifluoroacetic anhydride / CH₂Cl₂ / 0 °C

3: 61 percent / aq. HCl / methanol / 1 h / 20 °C

With pyridine; hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; trifluoroacetic anhydride; In methanol; dichloromethane; 2: Pummerer rearrangement;
DOI:10.1016/j.tet.2004.06.006

Reference yield:

: 592517-60-7
6-O-benzoyl-1,5-dideoxy-3,4-O-isopropylidene-2-O-methoxymethyl-5-thio-D-glucopyranose (S)-S-oxide

: 756485-46-8
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

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / NaOMe / methanol / 20 h / 20 °C

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

3: 51 percent / pyridine; trifluoroacetic anhydride / CH₂Cl₂ / 0 °C

4: 61 percent / aq. HCl / methanol / 1 h / 20 °C

With pyridine; hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; trifluoroacetic anhydride; In methanol; dichloromethane; 3: Pummerer rearrangement;
DOI:10.1016/j.tet.2004.06.006