1,5-dideoxy-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 (S)-S-oxide

Base Information

Chemical Name:1,5-dideoxy-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 (S)-S-oxide
CAS No.:756485-42-4
Molecular Formula:C₄₉H₆₂O₁₄S₂
Molecular Weight:939.155
Hs Code.:

1,5-dideoxy-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 (S)-S-oxide

Synonyms:1,5-dideoxy-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 (S)-S-oxide

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Chemical Property of 1,5-dideoxy-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 (S)-S-oxide

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Technology Process of 1,5-dideoxy-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 (S)-S-oxide

There total 2 articles about 1,5-dideoxy-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 (S)-S-oxide 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: 93.0%

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

: 756485-41-3
1,5-dideoxy-3,4-O-isopropylidene-2-O-methoxymethyl-5-thio-D-glucopyranose (S)-S-oxide

: 756485-42-4
1,5-dideoxy-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 (S)-S-oxide

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -78 - 20 ℃; for 2h;
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

: 756485-42-4
1,5-dideoxy-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 (S)-S-oxide

Guidance literature:: Multi-step reaction with 2 steps

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

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

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; In methanol; dichloromethane;
DOI:10.1016/j.tet.2004.06.006

Reference yield:

: 756485-42-4
1,5-dideoxy-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 (S)-S-oxide

: 756485-50-4
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

Guidance literature:: Multi-step reaction with 4 steps

1: 51 percent / pyridine; trifluoroacetic anhydride / CH₂Cl₂ / 0 °C

2: 61 percent / aq. HCl / methanol / 1 h / 20 °C

3: pyridine / CH₂Cl₂ / 33 h / 20 °C

4: 79 percent / hydrazine acetate / dimethylformamide / 12 h / 20 °C

With pyridine; hydrogenchloride; hydrazinium monoacetate; trifluoroacetic anhydride; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Pummerer rearrangement;
DOI:10.1016/j.tet.2004.06.006