7-O-(t-butyldiphenylsilyl)-1,2-dideoxy-5,6-O-isopropylidene-4-C-methyl-keto-D-arabino-3-heptulose

Base Information

Chemical Name:7-O-(t-butyldiphenylsilyl)-1,2-dideoxy-5,6-O-isopropylidene-4-C-methyl-keto-D-arabino-3-heptulose
CAS No.:105544-90-9
Molecular Formula:C₂₇H₃₈O₅Si
Molecular Weight:470.681
Hs Code.:

Synonyms:7-O-(t-butyldiphenylsilyl)-1,2-dideoxy-5,6-O-isopropylidene-4-C-methyl-keto-D-arabino-3-heptulose

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Chemical Property of 7-O-(t-butyldiphenylsilyl)-1,2-dideoxy-5,6-O-isopropylidene-4-C-methyl-keto-D-arabino-3-heptulose

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Technology Process of 7-O-(t-butyldiphenylsilyl)-1,2-dideoxy-5,6-O-isopropylidene-4-C-methyl-keto-D-arabino-3-heptulose

There total 10 articles about 7-O-(t-butyldiphenylsilyl)-1,2-dideoxy-5,6-O-isopropylidene-4-C-methyl-keto-D-arabino-3-heptulose 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%

: 105544-88-5,105616-51-1
(R)-2-[(4R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-pentane-2,3-diol

: 105544-90-9
7-O-(t-butyldiphenylsilyl)-1,2-dideoxy-5,6-O-isopropylidene-4-C-methyl-keto-D-arabino-3-heptulose

Guidance literature:: With dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In pyridine; benzene; for 5h; Ambient temperature;
DOI:10.1016/S0040-4039(00)84382-8

Reference yield:

: 67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1
2,3-O-isopropylidene-D-ribofuranose

: 105544-90-9
7-O-(t-butyldiphenylsilyl)-1,2-dideoxy-5,6-O-isopropylidene-4-C-methyl-keto-D-arabino-3-heptulose

Guidance literature:: Multi-step reaction with 9 steps

1: 73 percent / diethyl ether / 3 h / Ambient temperature

2: NaIO₄ / acetone; H₂O / 2 h / Ambient temperature

3: LiALH₄ / tetrahydrofuran / 2 h / Ambient temperature

4: imidasole / dimethylformamide / 1 h / Ambient temperature

5: 95 percent / PCC, 3A molecular sieves / CH₂Cl₂ / 2 h / Ambient temperature

6: 94 percent / tetrahydrofuran / 2 h / Ambient temperature

7: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2.) from -78 deg C to room temp.

8: diethyl ether / 1.5 h / Ambient temperature

9: 90 percent / DMSO, DCC, TFA / benzene; pyridine / 5 h / Ambient temperature

With 1H-imidazole; sodium periodate; lithium aluminium tetrahydride; dimethylsulfide; 3 A molecular sieve; ozone; dimethyl sulfoxide; dicyclohexyl-carbodiimide; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1016/S0040-4039(00)84382-8

Reference yield:

: 532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7
D-Ribose

: 105544-90-9
7-O-(t-butyldiphenylsilyl)-1,2-dideoxy-5,6-O-isopropylidene-4-C-methyl-keto-D-arabino-3-heptulose

Guidance literature:: Multi-step reaction with 10 steps

1: 83 percent / acetone, concd H₂SO₄ / 1.) 0 deg C, 3 h, 2.) 5 deg C, 20 h

2: 73 percent / diethyl ether / 3 h / Ambient temperature

3: NaIO₄ / acetone; H₂O / 2 h / Ambient temperature

4: LiALH₄ / tetrahydrofuran / 2 h / Ambient temperature

5: imidasole / dimethylformamide / 1 h / Ambient temperature

6: 95 percent / PCC, 3A molecular sieves / CH₂Cl₂ / 2 h / Ambient temperature

7: 94 percent / tetrahydrofuran / 2 h / Ambient temperature

8: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2.) from -78 deg C to room temp.

9: diethyl ether / 1.5 h / Ambient temperature

10: 90 percent / DMSO, DCC, TFA / benzene; pyridine / 5 h / Ambient temperature

With 1H-imidazole; sodium periodate; lithium aluminium tetrahydride; dimethylsulfide; 3 A molecular sieve; sulfuric acid; ozone; dimethyl sulfoxide; dicyclohexyl-carbodiimide; acetone; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1016/S0040-4039(00)84382-8