2,4,6-tri-O-benzyl-3,5-dideoxy-3,5-di-C-methyl-L-idose diethyl dithioacetal

Base Information

Chemical Name:2,4,6-tri-O-benzyl-3,5-dideoxy-3,5-di-C-methyl-L-idose diethyl dithioacetal
CAS No.:84247-26-7
Molecular Formula:C₃₃H₄₄O₃S₂
Molecular Weight:552.843
Hs Code.:

Synonyms:2,4,6-tri-O-benzyl-3,5-dideoxy-3,5-di-C-methyl-L-idose diethyl dithioacetal

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Chemical Property of 2,4,6-tri-O-benzyl-3,5-dideoxy-3,5-di-C-methyl-L-idose diethyl dithioacetal

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Technology Process of 2,4,6-tri-O-benzyl-3,5-dideoxy-3,5-di-C-methyl-L-idose diethyl dithioacetal

There total 23 articles about 2,4,6-tri-O-benzyl-3,5-dideoxy-3,5-di-C-methyl-L-idose diethyl dithioacetal 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: 74.0%

: 100-39-0
benzyl bromide

: 84247-25-6
3,5-dideoxy-3,5-di-C-methyl-L-idose diethyl dithioacetal

: 84247-26-7
2,4,6-tri-O-benzyl-3,5-dideoxy-3,5-di-C-methyl-L-idose diethyl dithioacetal

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; for 18h; Ambient temperature;
DOI:10.1016/0008-6215(82)84027-5

Reference yield:

: 3-deoxy-3-C-methyl-D-glucopyranose

: 84247-26-7
2,4,6-tri-O-benzyl-3,5-dideoxy-3,5-di-C-methyl-L-idose diethyl dithioacetal

Guidance literature:: Multi-step reaction with 10 steps

1: 24.1 g / anhydrous FeCl₃ / 2.5 h / Ambient temperature

2: 90percent aq. AcOH / 1.5 h / 60 °C

3: 85 percent / DMAP / pyridine / 0.42 h / 0 °C

4: 86 percent / Jones reagent / acetone / 1.5 h / Ambient temperature

5: 52 percent / 4M methylsulfinylmethanide anion/Me₂SO / diethyl ether / 0.25 h / Ambient temperature

6: 95 percent / 1M aq. NaOH / methanol / 0.25 h

7: 60 percent / 70percent aq. TFA / 2 h / Ambient temperature

8: 80 percent / H₂ / (Ph₃P)3RhCl / benzene / 3 h / Ambient temperature

9: 95 percent / BF₃*Et₂O / 1 h / Ambient temperature

10: 74 percent / NaH / dimethylformamide / 18 h / Ambient temperature

With dmap; sodium hydroxide; jones reagent; dimethyl sulfoxide; deprotonated form; boron trifluoride diethyl etherate; hydrogen; iron(III) chloride; sodium hydride; acetic acid; dimethyl sulfoxide; trifluoroacetic acid; Wilkinson's catalyst; In pyridine; methanol; diethyl ether; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1016/0008-6215(82)84027-5

Reference yield:

: 81114-49-0
3-deoxy-1,2-O-isopropylidene-3-C-methyl-α-D-glucofuranose

: 84247-26-7
2,4,6-tri-O-benzyl-3,5-dideoxy-3,5-di-C-methyl-L-idose diethyl dithioacetal

Guidance literature:: Multi-step reaction with 8 steps

1: 85 percent / DMAP / pyridine / 0.42 h / 0 °C

2: 86 percent / Jones reagent / acetone / 1.5 h / Ambient temperature

3: 52 percent / 4M methylsulfinylmethanide anion/Me₂SO / diethyl ether / 0.25 h / Ambient temperature

4: 95 percent / 1M aq. NaOH / methanol / 0.25 h

5: 60 percent / 70percent aq. TFA / 2 h / Ambient temperature

6: 80 percent / H₂ / (Ph₃P)3RhCl / benzene / 3 h / Ambient temperature

7: 95 percent / BF₃*Et₂O / 1 h / Ambient temperature

8: 74 percent / NaH / dimethylformamide / 18 h / Ambient temperature

With dmap; sodium hydroxide; jones reagent; dimethyl sulfoxide; deprotonated form; boron trifluoride diethyl etherate; hydrogen; sodium hydride; dimethyl sulfoxide; trifluoroacetic acid; Wilkinson's catalyst; In pyridine; methanol; diethyl ether; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1016/0008-6215(82)84027-5