1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erythro-pentitol

Base Information

Chemical Name:1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erythro-pentitol
CAS No.:848862-75-9
Molecular Formula:C₃₂H₄₀O₄Si
Molecular Weight:516.753
Hs Code.:

Synonyms:1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erythro-pentitol

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Chemical Property of 1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erythro-pentitol

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Technology Process of 1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erythro-pentitol

There total 10 articles about 1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erythro-pentitol 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: 93.4%

: 1779-49-3
Methyltriphenylphosphonium bromide

: 848862-73-7
1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-4-keto-D-erythro-pentitol

: 848862-75-9
1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erythro-pentitol

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at 20 ℃;
DOI:10.1021/ol006999c

Reference yield:

: 117174-48-8
1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-D-ribitol

: 848862-75-9
1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erythro-pentitol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 100 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -70 - 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C

2.2: 92 percent / tetrahydrofuran; hexane / 16 h / 20 °C

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1.1: Swern oxidation;
DOI:10.1016/j.tetasy.2004.11.069

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

: 848862-75-9
1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erythro-pentitol

Guidance literature:: Multi-step reaction with 9 steps

1.1: sulfuric acid / 2 h / 20 °C

1.2: 96 percent / acetone / 72 h / 20 °C

2.1: 61 percent / sodium hydride / dimethylformamide / 3 h / 0 °C

3.1: 92 percent / potassium tert-butoxide / dimethylsulfoxide / 16 h / 100 °C

4.1: ozone / CH₂Cl₂ / -78 °C

4.2: 95 percent / triphenylphsphine / CH₂Cl₂ / -78 - 20 °C

5.1: 100 percent / methanol; triethylamine / 16 h / 20 °C

6.1: 88 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 20 °C

7.1: 98 percent / imidazole / dimethylformamide / 16 h / 20 °C

8.1: 100 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -70 - 20 °C

9.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C

9.2: 92 percent / tetrahydrofuran; hexane / 16 h / 20 °C

With 1H-imidazole; methanol; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; sulfuric acid; potassium tert-butylate; sodium hydride; ozone; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 1.2: Fischer glycosidation / 8.1: Swern oxidation;
DOI:10.1016/j.tetasy.2004.11.069