methyl 2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-glucopyranoside

Base Information

Chemical Name:methyl 2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-glucopyranoside
CAS No.:84247-03-0
Molecular Formula:C₁₇H₂₂O₆
Molecular Weight:322.358
Hs Code.:

Synonyms:methyl 2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-glucopyranoside

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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-O-acetyl-4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-glucopyranoside

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Technology Process of methyl 2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-glucopyranoside

There total 1 articles about methyl 2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-glucopyranoside 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: 79.0%

: 108-24-7
acetic anhydride

: 73683-73-5
methyl 4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-glucopyranoside

: 84247-03-0
methyl 2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-glucopyranoside

Guidance literature:: With dmap; In pyridine; for 1.5h; Ambient temperature;
DOI:10.1016/0008-6215(82)84027-5

Reference yield:

: 84247-03-0
methyl 2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-glucopyranoside

: 84247-24-5
1-O-benzyl-2,4,7-trideoxy-2,4-di-C-methyl-D-glycero-L-ido-heptitol

Guidance literature:: Multi-step reaction with 19 steps

1: 67.3 g / NBS, BaCO₃ / CCl₄ / 23 h / 80 °C

2: LiAlH₄ / tetrahydrofuran / 2 h / 75 °C

3: 22.6 g / conc. H₂SO₄ / 1.5 h / Ambient temperature

4: 11.5 g / NaOH/MeOH / 3 h / Ambient temperature

5: 49 percent / anhydrous FeCl₃ / 5.5 h / Ambient temperature

6: 85 percent / 55percent NaH / tetrahydrofuran / 48 h / Ambient temperature

7: 91 percent / 50percent aq. AcOH / 1 h / Heating

8: 82 percent / Mg / diethyl ether / 20 h / Ambient temperature

9: 95 percent / anhydrous p-TsOH / dimethylformamide / 0.33 h / Ambient temperature

10: 96 percent / DMAP / ethyl acetate / 0.5 h / Ambient temperature

11: 622 mg / H₂ / Pd black / methanol / 0.25 h / Ambient temperature

12: pyridine / 0.33 h / Ambient temperature

13: 4.17M NaOMe/MeOH / CHCl₃ / 0.17 h

14: 22 percent / 1.64 BuLi/hexane / tetrahydrofuran / 72 h / 5 °C

15: 88 percent / DMAP / ethyl acetate / 0.5 h / Ambient temperature

16: 93 percent / HgO, HgCl₂ / acetone; H₂O / 0.33 h / 70 °C

17: 96 percent / LiAlH₄ / tetrahydrofuran / 0.17 h / Ambient temperature

18: 79 percent / NaH / tetrahydrofuran / Ambient temperature

19: 92 percent / 50percent difluoroacetic acid / 0.5 h / 0 °C

With methanol; Difluoroacetic acid; dmap; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; hexane; sulfuric acid; hydrogen; sodium methylate; iron(III) chloride; sodium hydride; toluene-4-sulfonic acid; magnesium; acetic acid; barium carbonate; mercury dichloride; mercury(II) oxide; palladium; In tetrahydrofuran; pyridine; methanol; tetrachloromethane; diethyl ether; chloroform; water; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1016/0008-6215(82)84027-5