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

Base Information

Chemical Name:tert-butyl 5-[methyl 2,3-di-O-benzyl-4-O-levulinoyl-α-D-glucopyranosid-6-yloxymethyl]-2-methylbenzoate
CAS No.:478977-52-5
Molecular Formula:C₃₉H₄₈O₁₀
Molecular Weight:676.804
Hs Code.:

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

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

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

There total 4 articles about tert-butyl 5-[methyl 2,3-di-O-benzyl-4-O-levulinoyl-α-D-glucopyranosid-6-yloxymethyl]-2-methylbenzoate 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: 75.0%

: 123-76-2
levulinic acid

: 522633-04-1
tert-butyl-5-[methyl 2,3-di-O-benzyl-α-D-glucopyranosid-6-yloxymethyl]-2-methylbenzoate

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

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 24h;
DOI:10.1002/1099-0690(200301)2003:1<128::AID-EJOC128>3.0.CO;2-S

Reference yield:

: 118-90-1
ortho-methylbenzoic acid

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

Guidance literature:: Multi-step reaction with 4 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

With dmap; phosphoric acid; boron trifluoride diethyl etherate; hydrogen bromide; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; dicyclohexyl-carbodiimide; 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

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

Guidance literature:: Multi-step reaction with 3 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

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