8-O-allyl-5-O-benzyl-6-deoxy-1,2-O-isopropylidene-3-O-<(methylthio)methyl>-α-D-glycero-L-talo-octofuranose-(1,4)

Base Information

Chemical Name:8-O-allyl-5-O-benzyl-6-deoxy-1,2-O-isopropylidene-3-O-<(methylthio)methyl>-α-D-glycero-L-talo-octofuranose-(1,4)
CAS No.:111690-04-1
Molecular Formula:C₂₃H₃₄O₇S
Molecular Weight:454.585
Hs Code.:

Synonyms:8-O-allyl-5-O-benzyl-6-deoxy-1,2-O-isopropylidene-3-O-<(methylthio)methyl>-α-D-glycero-L-talo-octofuranose-(1,4)

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Chemical Property of 8-O-allyl-5-O-benzyl-6-deoxy-1,2-O-isopropylidene-3-O-<(methylthio)methyl>-α-D-glycero-L-talo-octofuranose-(1,4)

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Technology Process of 8-O-allyl-5-O-benzyl-6-deoxy-1,2-O-isopropylidene-3-O-<(methylthio)methyl>-α-D-glycero-L-talo-octofuranose-(1,4)

There total 8 articles about 8-O-allyl-5-O-benzyl-6-deoxy-1,2-O-isopropylidene-3-O-<(methylthio)methyl>-α-D-glycero-L-talo-octofuranose-(1,4) 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: 86.0%

: 111690-02-9
5-O-benzyl-6-deoxy-1,2-O-isopropylidene-3-O-<(methylthio)methyl>-α-D-glycero-L-talo-octofuranose-(1,4)

: 106-95-6
allyl bromide

: 111690-04-1
8-O-allyl-5-O-benzyl-6-deoxy-1,2-O-isopropylidene-3-O-<(methylthio)methyl>-α-D-glycero-L-talo-octofuranose-(1,4)

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 5 ℃; for 36h;
DOI:10.1021/jo00237a011

Reference yield:

: 106180-08-9
5-deoxy-1,2-O-isopropylidene-3-O-<(methylthio)methyl>-5-nitro-α-D-ribofuranose

: 111690-04-1
8-O-allyl-5-O-benzyl-6-deoxy-1,2-O-isopropylidene-3-O-<(methylthio)methyl>-α-D-glycero-L-talo-octofuranose-(1,4)

Guidance literature:: Multi-step reaction with 8 steps

1: KF, n-Bu₄NI / toluene / 2 h / Ambient temperature

2: pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / Ambient temperature

3: NaBH₄, water / tetrahydrofuran / 12 h / Ambient temperature

4: 70 percent / H₂ / Raney-Ni / ethyl acetate / 48 h / 2844.3 Torr / Ambient temperature

5: 1.) 3,5-di-tert-butyl-1,2-benzoquinone, 2.) oxalic acid / 1.) MeOH, RT, 2 h, 2.) THF, 4 days, RT, pH 2

6: 32 percent / NaBH₄, water / tetrahydrofuran / 0.5 h

7: 100 percent / NaH / tetrahydrofuran / 1 h

8: 86 percent / NaH / tetrahydrofuran / 36 h / 5 °C

With pyridine; dmap; potassium fluoride; sodium tetrahydroborate; 3,5-di-tert-butyl-o-benzoquinone; water; hydrogen; oxalic acid; tetra-(n-butyl)ammonium iodide; sodium hydride; nickel; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/jo00237a011

Reference yield:

: 111689-96-4,111717-87-4
(3aR,5S,6R,6aR)-5-[2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-1-nitro-ethyl]-2,2-dimethyl-6-methylsulfanylmethoxy-tetrahydro-furo[2,3-d][1,3]dioxole

: 111690-04-1
8-O-allyl-5-O-benzyl-6-deoxy-1,2-O-isopropylidene-3-O-<(methylthio)methyl>-α-D-glycero-L-talo-octofuranose-(1,4)

Guidance literature:: Multi-step reaction with 5 steps

1: 70 percent / H₂ / Raney-Ni / ethyl acetate / 48 h / 2844.3 Torr / Ambient temperature

2: 1.) 3,5-di-tert-butyl-1,2-benzoquinone, 2.) oxalic acid / 1.) MeOH, RT, 2 h, 2.) THF, 4 days, RT, pH 2

3: 32 percent / NaBH₄, water / tetrahydrofuran / 0.5 h

4: 100 percent / NaH / tetrahydrofuran / 1 h

5: 86 percent / NaH / tetrahydrofuran / 36 h / 5 °C

With sodium tetrahydroborate; 3,5-di-tert-butyl-o-benzoquinone; water; hydrogen; oxalic acid; sodium hydride; nickel; In tetrahydrofuran; ethyl acetate;
DOI:10.1021/jo00237a011