methyl (phenyl 2-O-allyl-3-O-benzyl-4-O-triisopropylsilyl-1-thio-α-D-glucopyranoside) uronate

Base Information

Chemical Name:methyl (phenyl 2-O-allyl-3-O-benzyl-4-O-triisopropylsilyl-1-thio-α-D-glucopyranoside) uronate
CAS No.:635683-72-6
Molecular Formula:C₃₂H₄₆O₆SSi
Molecular Weight:586.865
Hs Code.:

Synonyms:methyl (phenyl 2-O-allyl-3-O-benzyl-4-O-triisopropylsilyl-1-thio-α-D-glucopyranoside) uronate

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Chemical Property of methyl (phenyl 2-O-allyl-3-O-benzyl-4-O-triisopropylsilyl-1-thio-α-D-glucopyranoside) uronate

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Technology Process of methyl (phenyl 2-O-allyl-3-O-benzyl-4-O-triisopropylsilyl-1-thio-α-D-glucopyranoside) uronate

There total 9 articles about methyl (phenyl 2-O-allyl-3-O-benzyl-4-O-triisopropylsilyl-1-thio-α-D-glucopyranoside) uronate 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: 91.0%

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 635683-70-4
methyl (phenyl 2-O-allyl-3-O-benzyl-1-thio-α-D-glucopyranoside) uronate

: 635683-72-6
methyl (phenyl 2-O-allyl-3-O-benzyl-4-O-triisopropylsilyl-1-thio-α-D-glucopyranoside) uronate

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; for 6h;
DOI:10.1021/ol035606h

Reference yield:

: 4551-15-9
phenylthiotrimethylsilane

: 635683-72-6
methyl (phenyl 2-O-allyl-3-O-benzyl-4-O-triisopropylsilyl-1-thio-α-D-glucopyranoside) uronate

Guidance literature:: Multi-step reaction with 4 steps

1.1: ZnI₂ / CH₂Cl₂ / 2.5 h / 0 - 20 °C

1.2: TBAF / tetrahydrofuran / 0.5 h

2.1: 85 percent / pyridinium dichromate; Ac₂O / CH₂Cl₂ / 5 h

3.1: 76 percent / AcCl / 12 h

4.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 6 h

With 2,6-dimethylpyridine; dipyridinium dichromate; acetic anhydride; acetyl chloride; zinc(II) iodide; In dichloromethane;
DOI:10.1021/ol035606h

Reference yield:

: 100-39-0
benzyl bromide

: 635683-72-6
methyl (phenyl 2-O-allyl-3-O-benzyl-4-O-triisopropylsilyl-1-thio-α-D-glucopyranoside) uronate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 83 percent / NaH / dimethylformamide / 0.75 h

2.1: ZnI₂ / CH₂Cl₂ / 2.5 h / 0 - 20 °C

2.2: TBAF / tetrahydrofuran / 0.5 h

3.1: 85 percent / pyridinium dichromate; Ac₂O / CH₂Cl₂ / 5 h

4.1: 76 percent / AcCl / 12 h

5.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 6 h

With 2,6-dimethylpyridine; dipyridinium dichromate; acetic anhydride; sodium hydride; acetyl chloride; zinc(II) iodide; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol035606h