5-[methyl 2,3-di-O-benzyl-4-O-levulinoyl-α-D-glucopyranosid-6-yloxymethyl]-2-methylbenzoic acid

Base Information

Chemical Name:5-[methyl 2,3-di-O-benzyl-4-O-levulinoyl-α-D-glucopyranosid-6-yloxymethyl]-2-methylbenzoic acid
CAS No.:478977-54-7
Molecular Formula:C₃₅H₄₀O₁₀
Molecular Weight:620.697
Hs Code.:

Synonyms:5-[methyl 2,3-di-O-benzyl-4-O-levulinoyl-α-D-glucopyranosid-6-yloxymethyl]-2-methylbenzoic acid

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Chemical Property of 5-[methyl 2,3-di-O-benzyl-4-O-levulinoyl-α-D-glucopyranosid-6-yloxymethyl]-2-methylbenzoic acid

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Technology Process of 5-[methyl 2,3-di-O-benzyl-4-O-levulinoyl-α-D-glucopyranosid-6-yloxymethyl]-2-methylbenzoic acid

There total 5 articles about 5-[methyl 2,3-di-O-benzyl-4-O-levulinoyl-α-D-glucopyranosid-6-yloxymethyl]-2-methylbenzoic acid 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: 90.0%

: 478977-52-5
tert-butyl 5-[methyl 2,3-di-O-benzyl-4-O-levulinoyl-α-D-glucopyranosid-6-yloxymethyl]-2-methylbenzoate

: 478977-54-7
5-[methyl 2,3-di-O-benzyl-4-O-levulinoyl-α-D-glucopyranosid-6-yloxymethyl]-2-methylbenzoic acid

Guidance literature:: With trifluoroacetic acid; In dichloromethane; for 4h;
DOI:10.1002/1099-0690(200301)2003:1<128::AID-EJOC128>3.0.CO;2-S

Reference yield:

: 118-90-1
ortho-methylbenzoic acid

: 478977-54-7
5-[methyl 2,3-di-O-benzyl-4-O-levulinoyl-α-D-glucopyranosid-6-yloxymethyl]-2-methylbenzoic acid

Guidance literature:: Multi-step reaction with 5 steps

1: 62 percent / HBr; o-phosphoric acid / acetic acid / 3 h / 115 °C

2: BF₃*Et₂O / CH₂Cl₂; cyclohexane / 1 h / 20 °C

3: 70 percent / Bu₂SnO; TBAI / toluene / 11 h / Heating

4: 75 percent / DCC; DMAP / CH₂Cl₂ / 24 h

5: 90 percent / TFA / CH₂Cl₂ / 4 h

With dmap; phosphoric acid; boron trifluoride diethyl etherate; hydrogen bromide; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane; cyclohexane; acetic acid; toluene;
DOI:10.1002/1099-0690(200301)2003:1<128::AID-EJOC128>3.0.CO;2-S

Reference yield:

: 72985-19-4
5-(bromomethyl)-2-methylbenzoic acid

: 478977-54-7
5-[methyl 2,3-di-O-benzyl-4-O-levulinoyl-α-D-glucopyranosid-6-yloxymethyl]-2-methylbenzoic acid

Guidance literature:: Multi-step reaction with 4 steps

1: BF₃*Et₂O / CH₂Cl₂; cyclohexane / 1 h / 20 °C

2: 70 percent / Bu₂SnO; TBAI / toluene / 11 h / Heating

3: 75 percent / DCC; DMAP / CH₂Cl₂ / 24 h

4: 90 percent / TFA / CH₂Cl₂ / 4 h

With dmap; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane; cyclohexane; toluene;
DOI:10.1002/1099-0690(200301)2003:1<128::AID-EJOC128>3.0.CO;2-S