methyl 2'-O-allyl-3'-O-benzyl-4'-O-triisopropylsilyl-β-D-glucopyranosyluronate-(1->3)-1,6-dianhydro-4-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranose

Base Information

Chemical Name:methyl 2'-O-allyl-3'-O-benzyl-4'-O-triisopropylsilyl-β-D-glucopyranosyluronate-(1->3)-1,6-dianhydro-4-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranose
CAS No.:635683-73-7
Molecular Formula:C₄₇H₅₉NO₁₂Si
Molecular Weight:858.07
Hs Code.:

methyl 2'-O-allyl-3'-O-benzyl-4'-O-triisopropylsilyl-β-D-glucopyranosyluronate-(1->3)-1,6-dianhydro-4-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranose

Synonyms:methyl 2'-O-allyl-3'-O-benzyl-4'-O-triisopropylsilyl-β-D-glucopyranosyluronate-(1->3)-1,6-dianhydro-4-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranose

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Chemical Property of methyl 2'-O-allyl-3'-O-benzyl-4'-O-triisopropylsilyl-β-D-glucopyranosyluronate-(1->3)-1,6-dianhydro-4-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranose

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Technology Process of methyl 2'-O-allyl-3'-O-benzyl-4'-O-triisopropylsilyl-β-D-glucopyranosyluronate-(1->3)-1,6-dianhydro-4-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranose

There total 13 articles about methyl 2'-O-allyl-3'-O-benzyl-4'-O-triisopropylsilyl-β-D-glucopyranosyluronate-(1->3)-1,6-dianhydro-4-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranose 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: 60.0%

: 75347-74-9
1,6-anhydro-4-O-benzyl-2-desoxy-2-phthalimido-β-D-galactopyranose

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

: 635683-73-7
methyl 2'-O-allyl-3'-O-benzyl-4'-O-triisopropylsilyl-β-D-glucopyranosyluronate-(1->3)-1,6-dianhydro-4-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranose

: (2S,3S,4R,5R,6S)-5-Allyloxy-4-benzyloxy-6-[(1R,2R,3R,4R,5R)-2-benzyloxy-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6,8-dioxa-bicyclo[3.2.1]oct-3-yloxy]-3-triisopropylsilanyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: With N-iodo-succinimide; 4 A molecular sieve; trifluoroacetic acid; In dichloromethane; acetonitrile; at -40 - 20 ℃; for 3h;
DOI:10.1021/ol035606h

Reference yield:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 635683-73-7
methyl 2'-O-allyl-3'-O-benzyl-4'-O-triisopropylsilyl-β-D-glucopyranosyluronate-(1->3)-1,6-dianhydro-4-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranose

Guidance literature:: Multi-step reaction with 2 steps

1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 6 h

2: 60 percent / NIS; molecular sieves 4 Angstroem; TFA / CH₂Cl₂; acetonitrile / 3 h / -40 - 20 °C

With 2,6-dimethylpyridine; N-iodo-succinimide; 4 A molecular sieve; trifluoroacetic acid; In dichloromethane; acetonitrile;
DOI:10.1021/ol035606h

Reference yield:

: 100-39-0
benzyl bromide

: 635683-73-7
methyl 2'-O-allyl-3'-O-benzyl-4'-O-triisopropylsilyl-β-D-glucopyranosyluronate-(1->3)-1,6-dianhydro-4-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranose

Guidance literature:: Multi-step reaction with 6 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

6.1: 60 percent / NIS; molecular sieves 4 Angstroem; TFA / CH₂Cl₂; acetonitrile / 3 h / -40 - 20 °C

With 2,6-dimethylpyridine; N-iodo-succinimide; dipyridinium dichromate; 4 A molecular sieve; acetic anhydride; sodium hydride; acetyl chloride; trifluoroacetic acid; zinc(II) iodide; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ol035606h