methyl 6-O-[2',3',4'-[tris-O-(4-methoxyphenyl)methyl]-5'-deoxy-5'-thio-α-D-glucopyranosyl]-2,3,4-tri-O-benzoyl-α-D-glucopyranoside

Base Information

Chemical Name:methyl 6-O-[2',3',4'-[tris-O-(4-methoxyphenyl)methyl]-5'-deoxy-5'-thio-α-D-glucopyranosyl]-2,3,4-tri-O-benzoyl-α-D-glucopyranoside
CAS No.:565462-90-0
Molecular Formula:C₅₈H₆₀O₁₆S
Molecular Weight:1045.17
Hs Code.:

Synonyms:methyl 6-O-[2',3',4'-[tris-O-(4-methoxyphenyl)methyl]-5'-deoxy-5'-thio-α-D-glucopyranosyl]-2,3,4-tri-O-benzoyl-α-D-glucopyranoside

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Chemical Property of methyl 6-O-[2',3',4'-[tris-O-(4-methoxyphenyl)methyl]-5'-deoxy-5'-thio-α-D-glucopyranosyl]-2,3,4-tri-O-benzoyl-α-D-glucopyranoside

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Technology Process of methyl 6-O-[2',3',4'-[tris-O-(4-methoxyphenyl)methyl]-5'-deoxy-5'-thio-α-D-glucopyranosyl]-2,3,4-tri-O-benzoyl-α-D-glucopyranoside

There total 14 articles about methyl 6-O-[2',3',4'-[tris-O-(4-methoxyphenyl)methyl]-5'-deoxy-5'-thio-α-D-glucopyranosyl]-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 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: 71.0%

: 565462-89-7
methyl 6-[2',3',4'-tris-O-(4-methoxyphenyl)methyl-6'-O-(triphenyl)methyl-5'-deoxy-5'-thio-α-D-glucopyranosyl]-2,3,4-tri-O-benzoyl-α-D-glucopyranoside

: 565462-90-0
methyl 6-O-[2',3',4'-[tris-O-(4-methoxyphenyl)methyl]-5'-deoxy-5'-thio-α-D-glucopyranosyl]-2,3,4-tri-O-benzoyl-α-D-glucopyranoside

Guidance literature:: With toluene-4-sulfonic acid; In tetrahydrofuran; methanol;
DOI:10.1016/S0960-894X(03)00072-6

Reference yield:

: 137886-82-9
2,3,4,6-Tetra-O-acetyl-5-thio-α-D-glucopyranose

: 565462-90-0
methyl 6-O-[2',3',4'-[tris-O-(4-methoxyphenyl)methyl]-5'-deoxy-5'-thio-α-D-glucopyranosyl]-2,3,4-tri-O-benzoyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 95 percent / p-TsOH / CH₂Cl₂ / 1.5 h / 0 °C

2: 82 percent / NaOMe / methanol / 3.5 h / 20 °C

3: 80 percent / 4-(dimethylamino)pyridine; pyridine / 24 h / 20 °C

4: 56 percent / NaH / dimethylformamide / 20 °C

5: 16 percent / p-TsOH / ethanol / 7 h / 20 °C

6: 82 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.67 h / 0 °C

7: 67 percent / triethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 2 h / -78 °C

8: 71 percent / p-TsOH / methanol; tetrahydrofuran / 5 h / 20 °C

With pyridine; dmap; triethylsilyl trifluoromethyl sulfonate; sodium methylate; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2005.05.028

Reference yield:

: 2746-25-0
p-Methoxybenzyl bromide

: 565462-90-0
methyl 6-O-[2',3',4'-[tris-O-(4-methoxyphenyl)methyl]-5'-deoxy-5'-thio-α-D-glucopyranosyl]-2,3,4-tri-O-benzoyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 62 percent / NaH / dimethylformamide; toluene / 20 °C

2: 92 percent / pyridinium 4-toluenesulfonate / ethanol; propan-1-ol / 2.5 h / 20 °C

3: 82 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.67 h / 0 °C

4: 67 percent / triethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 2 h / -78 °C

5: 71 percent / p-TsOH / methanol; tetrahydrofuran / 5 h / 20 °C

With triethylsilyl trifluoromethyl sulfonate; pyridinium p-toluenesulfonate; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; propan-1-ol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.bmc.2005.05.028