1-O-benzyl-8-O-tert-butyldiphenylsilyl-2,3-dideoxy-4,5-O-isopropylidene-6-O-<(methylthio)thiocarbonyl>-α-L-xylo-oct-4-ulofuranose

Base Information

Chemical Name:1-O-benzyl-8-O-tert-butyldiphenylsilyl-2,3-dideoxy-4,5-O-isopropylidene-6-O-<(methylthio)thiocarbonyl>-α-L-xylo-oct-4-ulofuranose
CAS No.:159299-76-0
Molecular Formula:C₃₆H₄₆O₆S₂Si
Molecular Weight:666.975
Hs Code.:

Synonyms:1-O-benzyl-8-O-tert-butyldiphenylsilyl-2,3-dideoxy-4,5-O-isopropylidene-6-O-<(methylthio)thiocarbonyl>-α-L-xylo-oct-4-ulofuranose

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Chemical Property of 1-O-benzyl-8-O-tert-butyldiphenylsilyl-2,3-dideoxy-4,5-O-isopropylidene-6-O-<(methylthio)thiocarbonyl>-α-L-xylo-oct-4-ulofuranose

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Technology Process of 1-O-benzyl-8-O-tert-butyldiphenylsilyl-2,3-dideoxy-4,5-O-isopropylidene-6-O-<(methylthio)thiocarbonyl>-α-L-xylo-oct-4-ulofuranose

There total 8 articles about 1-O-benzyl-8-O-tert-butyldiphenylsilyl-2,3-dideoxy-4,5-O-isopropylidene-6-O-<(methylthio)thiocarbonyl>-α-L-xylo-oct-4-ulofuranose 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%

: 75-15-0,12122-00-8
carbon disulfide

: 159299-75-9
1-O-benzyl-8-O-tert-butyldiphenylsilyl-2,3-dideoxy-4,5-O-isopropylidene-α-L-xylo-oct-4-ulofuranose

: 74-88-4
methyl iodide

: 159299-76-0
1-O-benzyl-8-O-tert-butyldiphenylsilyl-2,3-dideoxy-4,5-O-isopropylidene-6-O-<(methylthio)thiocarbonyl>-α-L-xylo-oct-4-ulofuranose

Guidance literature:: With 1H-imidazole; sodium hydride; In tetrahydrofuran; for 1.25h; Ambient temperature;
DOI:10.1016/0008-6215(94)84020-2

Reference yield:

: 17682-70-1
2,3:4,6-bis-O-isopropylidene-L-sorbose

: 159299-76-0
1-O-benzyl-8-O-tert-butyldiphenylsilyl-2,3-dideoxy-4,5-O-isopropylidene-6-O-<(methylthio)thiocarbonyl>-α-L-xylo-oct-4-ulofuranose

Guidance literature:: Multi-step reaction with 8 steps

1: pyridinium chlorochromate, 4A sieves / CH₂Cl₂ / 12 h / Ambient temperature

2: CH₂Cl₂ / 24 h / Ambient temperature

3: 83 percent / H₂ / 10percent Pd/C / methanol / 4 h / 3040 Torr

4: 85 percent / LiAlH₄ / tetrahydrofuran / 7 h / Heating

5: t-BuOK / 1.) THF, RT, 0.5 h, 2.) THF, RT, 1 h

6: 100 percent / 50percent AcOH / 1 h / 50 °C

7: 100 percent / DMAP, Et₃N / CH₂Cl₂ / 16 h / Ambient temperature

8: 90 percent / NaH, imidazole / tetrahydrofuran / 1.25 h / Ambient temperature

With 1H-imidazole; dmap; lithium aluminium tetrahydride; 4 A molecular sieve; potassium tert-butylate; hydrogen; sodium hydride; acetic acid; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/0008-6215(94)84020-2

Reference yield:

: 55385-72-3
(3aS,3bR,7aS,8aR)-2,2,5,5-tetramethyltetrahydro-8aH-[1,3]dioxolo[4′,5′:4,5]furo[3,2-d][1,3]dioxine-8a-carbaldehyde

: 159299-76-0
1-O-benzyl-8-O-tert-butyldiphenylsilyl-2,3-dideoxy-4,5-O-isopropylidene-6-O-<(methylthio)thiocarbonyl>-α-L-xylo-oct-4-ulofuranose

Guidance literature:: Multi-step reaction with 7 steps

1: CH₂Cl₂ / 24 h / Ambient temperature

2: 83 percent / H₂ / 10percent Pd/C / methanol / 4 h / 3040 Torr

3: 85 percent / LiAlH₄ / tetrahydrofuran / 7 h / Heating

4: t-BuOK / 1.) THF, RT, 0.5 h, 2.) THF, RT, 1 h

5: 100 percent / 50percent AcOH / 1 h / 50 °C

6: 100 percent / DMAP, Et₃N / CH₂Cl₂ / 16 h / Ambient temperature

7: 90 percent / NaH, imidazole / tetrahydrofuran / 1.25 h / Ambient temperature

With 1H-imidazole; dmap; lithium aluminium tetrahydride; potassium tert-butylate; hydrogen; sodium hydride; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/0008-6215(94)84020-2