methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-methylene-α-D-arabino-hexopyranosid

Base Information

Chemical Name:methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-methylene-α-D-arabino-hexopyranosid
CAS No.:142644-81-3
Molecular Formula:C₂₂H₂₄O₅
Molecular Weight:368.43
Hs Code.:

Synonyms:methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-methylene-α-D-arabino-hexopyranosid

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Chemical Property of methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-methylene-α-D-arabino-hexopyranosid

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Technology Process of methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-methylene-α-D-arabino-hexopyranosid

There total 10 articles about methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-methylene-α-D-arabino-hexopyranosid 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: 89.0%

: 100-39-0
benzyl bromide

: 942041-33-0
methyl 4,6-O-benzylidene-2-C-methylene-α-D-arabino-hexopyranoside

: 142644-81-3
methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-methylene-α-D-arabino-hexopyranosid

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 1h;
DOI:10.1016/j.tetlet.2007.03.031

Reference yield:

: 942041-32-9
C₂₀H₂₆O₆

: 142644-81-3
methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-methylene-α-D-arabino-hexopyranosid

Guidance literature:: Multi-step reaction with 2 steps

1: 91 percent / AcOH; water / tetrahydrofuran / 1 h / 50 °C

2: 89 percent / NaH / dimethylformamide / 1 h / 20 °C

With water; sodium hydride; acetic acid; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2007.03.031

Reference yield:

: 3162-96-7
methyl 4,6-O-benzylidene-α-D-glucopyranoside

: 142644-81-3
methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-methylene-α-D-arabino-hexopyranosid

Guidance literature:: Multi-step reaction with 7 steps

1.1: Bu₂SnO / toluene; methanol / 14 h / 55 °C

1.2: Et₃N / dioxane / 4 h / 20 °C

2.1: 95 percent / P-TsOH / CH₂Cl₂ / 1 h / 20 °C

3.1: 96 percent / NaOMe / methanol / 2 h / 20 °C

4.1: TFAA; DMSO; Et₃N / CH₂Cl₂ / -78 °C

5.1: n-BuLi / tetrahydrofuran / -78 °C

6.1: 91 percent / AcOH; water / tetrahydrofuran / 1 h / 50 °C

7.1: 89 percent / NaH / dimethylformamide / 1 h / 20 °C

With n-butyllithium; water; sodium methylate; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 5.1: Wittig reaction;
DOI:10.1016/j.tetlet.2007.03.031