6-bromo-1,6-dideoxy-1,1-ethylenedioxy-2,3,4-tri-O-methyl-6-phenyl-D-glucopyranose

Base Information

Chemical Name:6-bromo-1,6-dideoxy-1,1-ethylenedioxy-2,3,4-tri-O-methyl-6-phenyl-D-glucopyranose
CAS No.:213968-31-1
Molecular Formula:C₁₇H₂₃BrO₆
Molecular Weight:403.27
Hs Code.:

Synonyms:6-bromo-1,6-dideoxy-1,1-ethylenedioxy-2,3,4-tri-O-methyl-6-phenyl-D-glucopyranose

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Chemical Property of 6-bromo-1,6-dideoxy-1,1-ethylenedioxy-2,3,4-tri-O-methyl-6-phenyl-D-glucopyranose

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Technology Process of 6-bromo-1,6-dideoxy-1,1-ethylenedioxy-2,3,4-tri-O-methyl-6-phenyl-D-glucopyranose

There total 9 articles about 6-bromo-1,6-dideoxy-1,1-ethylenedioxy-2,3,4-tri-O-methyl-6-phenyl-D-glucopyranose 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: 83.0%

: 7381-30-8
2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane

: 213968-30-0
(3R,4S,5S,6S)-6-(Bromo-phenyl-methyl)-3,4,5-trimethoxy-tetrahydro-pyran-2-one

: 213968-31-1
6-bromo-1,6-dideoxy-1,1-ethylenedioxy-2,3,4-tri-O-methyl-6-phenyl-D-glucopyranose

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 - 25 ℃; for 3h;
DOI:10.1071/C97156

Reference yield:

: 53958-71-7
methyl 2,3,4-tri-O-methyl-α-D-gluco-hexodialdo-1,5-pyranoside

: 213968-31-1
6-bromo-1,6-dideoxy-1,1-ethylenedioxy-2,3,4-tri-O-methyl-6-phenyl-D-glucopyranose

Guidance literature:: Multi-step reaction with 7 steps

1: 55 percent / diethyl ether / 2 h / Ambient temperature

2: 86 percent / Et₃N / CH₂Cl₂ / 4 h / 0 °C

3: 80 percent / LiBr / butan-2-one / 3 h / Heating

4: 82 percent / conc. sulfuric acid / acetic acid / 24 h / Ambient temperature

5: 71 percent / LiALH₄ / diethyl ether / 5 h / -40 °C

6: 86 percent / DMSO, (COCl)2 / CH₂Cl₂ / 0.75 h / -60 - 25 °C

7: 83 percent / trimethylsilyl triflate / CH₂Cl₂ / 3 h / 0 - 25 °C

With lithium aluminium tetrahydride; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; dimethyl sulfoxide; triethylamine; lithium bromide; In diethyl ether; dichloromethane; acetic acid; butanone;
DOI:10.1071/C97156

Reference yield:

: 213968-26-4
methyl 6-bromo-6-deoxy-2,3,4-tri-O-methyl-6-phenyl-α-D-glucopyranoside

: 213968-31-1
6-bromo-1,6-dideoxy-1,1-ethylenedioxy-2,3,4-tri-O-methyl-6-phenyl-D-glucopyranose

Guidance literature:: Multi-step reaction with 4 steps

1: 82 percent / conc. sulfuric acid / acetic acid / 24 h / Ambient temperature

2: 71 percent / LiALH₄ / diethyl ether / 5 h / -40 °C

3: 86 percent / DMSO, (COCl)2 / CH₂Cl₂ / 0.75 h / -60 - 25 °C

4: 83 percent / trimethylsilyl triflate / CH₂Cl₂ / 3 h / 0 - 25 °C

With lithium aluminium tetrahydride; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; dimethyl sulfoxide; In diethyl ether; dichloromethane; acetic acid;
DOI:10.1071/C97156