methyl-2-C-benzyloxy-3-deoxy-3-C-benzyloxymethyl-5-methylene-ribo-hexofuranoside

Base Information

Chemical Name:methyl-2-C-benzyloxy-3-deoxy-3-C-benzyloxymethyl-5-methylene-ribo-hexofuranoside
CAS No.:934279-78-4
Molecular Formula:C₂₂H₂₆O₄
Molecular Weight:354.446
Hs Code.:

Synonyms:methyl-2-C-benzyloxy-3-deoxy-3-C-benzyloxymethyl-5-methylene-ribo-hexofuranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of methyl-2-C-benzyloxy-3-deoxy-3-C-benzyloxymethyl-5-methylene-ribo-hexofuranoside

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Technology Process of methyl-2-C-benzyloxy-3-deoxy-3-C-benzyloxymethyl-5-methylene-ribo-hexofuranoside

There total 10 articles about methyl-2-C-benzyloxy-3-deoxy-3-C-benzyloxymethyl-5-methylene-ribo-hexofuranoside 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%

: methyl-2-hydroxy-3-deoxy-3-C-benzyloxymethyl-5-methylene-α-D-ribo-hexofuranoside

: 100-39-0
benzyl bromide

: 934279-78-4
methyl-2-C-benzyloxy-3-deoxy-3-C-benzyloxymethyl-5-methylene-ribo-hexofuranoside

Guidance literature:: methyl-2-hydroxy-3-deoxy-3-C-benzyloxymethyl-5-methylene-α-D-ribo-hexofuranoside; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;
DOI:10.1016/j.tet.2007.01.037

Reference yield:

: 3-deoxy-3-C-benzyloxymethyl-5,6-di-p-toluene-sulfonyl-oxy-1,2-O-isopropylidene-α-D-allofuranose

: 934279-78-4
methyl-2-C-benzyloxy-3-deoxy-3-C-benzyloxymethyl-5-methylene-ribo-hexofuranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 83 percent / sodium iodide; zinc / dimethylformamide / 4 h / Heating

2.1: 88 percent / amberlyst IR-120 (H⁺) resin / methanol / 3 h / Heating

3.1: NaH / dimethylformamide / 0.5 h / 20 °C

3.2: 90 percent / dimethylformamide / 0.5 h / 20 °C

With amberlyst IR-120 (H⁺) resin; sodium hydride; sodium iodide; zinc; In methanol; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2007.01.037

Reference yield:

: 2280-44-6
D-Glucose

: 934279-78-4
methyl-2-C-benzyloxy-3-deoxy-3-C-benzyloxymethyl-5-methylene-ribo-hexofuranoside

Guidance literature:: Multi-step reaction with 10 steps

1.1: H₂SO₄; CuSO₄ / 20 °C

2.1: PDC; Ac₂O / CH₂Cl₂ / 20 °C

3.1: NaNH₂ / tetrahydrofuran; H₂O / -20 - 20 °C

4.1: BH₃*Me₂S / tetrahydrofuran / 0 - 20 °C

4.2: aq. NaOH; H₂O₂ / tetrahydrofuran / 20 °C

5.1: NaH / tetrahydrofuran; dimethylformamide; various solvent(s) / 0.5 h / 20 °C

5.2: 93 percent / Bu₄NI / tetrahydrofuran; dimethylformamide; various solvent(s) / 3 h / 20 °C

6.1: 95 percent / aq. H₂SO₄ / methanol / 10 h / 20 °C

7.1: 92 percent / pyridine / 24 h / 20 °C

8.1: 83 percent / sodium iodide; zinc / dimethylformamide / 4 h / Heating

9.1: 88 percent / amberlyst IR-120 (H⁺) resin / methanol / 3 h / Heating

10.1: NaH / dimethylformamide / 0.5 h / 20 °C

10.2: 90 percent / dimethylformamide / 0.5 h / 20 °C

With dipyridinium dichromate; dimethylsulfide borane complex; amberlyst IR-120 (H⁺) resin; sulfuric acid; acetic anhydride; sodium hydride; sodium amide; copper(II) sulfate; sodium iodide; zinc; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2007.01.037