dibutyl (methyl 3-O-benzyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosid)uronate phosphate

Base Information

• Chemical Name: dibutyl (methyl 3-O-benzyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosid)uronate phosphate
• CAS No.: 373606-40-7
• Molecular Formula: C₂₈H₄₉O₁₀PSi
• Molecular Weight: 604.75

Synonyms:dibutyl (methyl 3-O-benzyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosid)uronate phosphate

Chemical Property of dibutyl (methyl 3-O-benzyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosid)uronate phosphate

Chemical Property:

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Technology Process of dibutyl (methyl 3-O-benzyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosid)uronate phosphate

There total 2 articles about dibutyl (methyl 3-O-benzyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosid)uronate phosphate 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:

4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydro-2H-pyran-2-carboxylic acid methyl ester (356067-98-6) → dibutyl (methyl 3-O-benzyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosid)uronate phosphate (373606-40-7)

Guidance literature:

Multi-step reaction with 2 steps

1: dimethyldioxirane / CH₂Cl₂; toluene; acetone / 1 h / 0 °C

2: CH₂Cl₂ / 3.5 h / -78 - 0 °C

With 3,3-dimethyldioxirane; In dichloromethane; acetone; toluene;

DOI:10.1021/ja016227r

Reference yield:

(3S,4S,5R)-5-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2,7-dioxa-bicyclo[4.1.0]heptane-3-carboxylic acid methyl ester + dibutyl phosphate (107-66-4) → dibutyl (methyl 3-O-benzyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosid)uronate phosphate (373606-40-7)

Guidance literature:

In dichloromethane; at -78 - 0 ℃; for 3.5h;

DOI:10.1021/ja016227r

Reference yield: 65.0%

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) + dibutyl (methyl 3-O-benzyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosid)uronate phosphate (373606-40-7) → methyl 3-O-benzyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -60 ℃; for 0.25h;

DOI:10.1021/ja016227r

upstream raw materials:

dibutyl phosphate

4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydro-2H-pyran-2-carboxylic acid methyl ester

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