1D-(1,3/2,4)-1-O-t-butyldimethylsilyl-4-hydroxymethyl-5-cyclohexene-1,2,3-triol

Base Information

Chemical Name:1D-(1,3/2,4)-1-O-t-butyldimethylsilyl-4-hydroxymethyl-5-cyclohexene-1,2,3-triol
CAS No.:155193-82-1
Molecular Formula:C₁₃H₂₆O₄Si
Molecular Weight:274.433
Hs Code.:

Synonyms:1D-(1,3/2,4)-1-O-t-butyldimethylsilyl-4-hydroxymethyl-5-cyclohexene-1,2,3-triol

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Chemical Property of 1D-(1,3/2,4)-1-O-t-butyldimethylsilyl-4-hydroxymethyl-5-cyclohexene-1,2,3-triol

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Technology Process of 1D-(1,3/2,4)-1-O-t-butyldimethylsilyl-4-hydroxymethyl-5-cyclohexene-1,2,3-triol

There total 10 articles about 1D-(1,3/2,4)-1-O-t-butyldimethylsilyl-4-hydroxymethyl-5-cyclohexene-1,2,3-triol 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: 80.0%

: 155193-80-9
1D-(1,3/2,4)-4-acetoxymethyl-3-O-acetyl-2-O-benzoyl-1-O-t-butyldimethylsilyl-5-cyclohexene-1,2,3-triol

: 155193-82-1
1D-(1,3/2,4)-1-O-t-butyldimethylsilyl-4-hydroxymethyl-5-cyclohexene-1,2,3-triol

Guidance literature:: With potassium hydroxide; In ethanol; for 0.333333h; Ambient temperature; pH=10;
DOI:10.1246/cl.1994.37

Reference yield:

: 38993-01-0
methyl 3-O-benzoyl-4,6-O-benzylidene-α-D-arabino-hexopyranosid-2-ulose

: 155193-82-1
1D-(1,3/2,4)-1-O-t-butyldimethylsilyl-4-hydroxymethyl-5-cyclohexene-1,2,3-triol

Guidance literature:: Multi-step reaction with 10 steps

1: 82 percent / LDA / tetrahydrofuran / -78 °C

2: 82 percent / NaBH₄ / dimethylsulfoxide / 80 °C

3: 100 percent / pyridine / Ambient temperature

4: NBS, BaCO₃ / CCl₄ / Heating

5: NaI / acetone / Heating

6: DBU, MS-4A / dimethylsulfoxide / 1 h / 80 °C

7: 1.) HgCl₂, 2.) Et₃N / 1.) acetone-H₂O, reflux, 1 h, 2.) CH₂Cl₂, 0 deg C

8: 67 percent / NaBH₄, CeCl₃*7H₂O / ethanol; CH₂Cl₂ / -78 °C

9: 94 percent / imidazole / dimethylformamide / 40 °C

10: 80 percent / KOH / ethanol / 0.33 h / Ambient temperature; pH=10

With pyridine; 1H-imidazole; potassium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; cerium(III) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; barium carbonate; sodium iodide; mercury dichloride; lithium diisopropyl amide; In tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;
DOI:10.1246/cl.1994.37

Reference yield:

: 155193-75-2
methyl 4,6-O-benzylidene-2-deoxy-2-C-hydroxymethyl-α-D-glucopyranoside

: 155193-82-1
1D-(1,3/2,4)-1-O-t-butyldimethylsilyl-4-hydroxymethyl-5-cyclohexene-1,2,3-triol

Guidance literature:: Multi-step reaction with 8 steps

1: 100 percent / pyridine / Ambient temperature

2: NBS, BaCO₃ / CCl₄ / Heating

3: NaI / acetone / Heating

4: DBU, MS-4A / dimethylsulfoxide / 1 h / 80 °C

5: 1.) HgCl₂, 2.) Et₃N / 1.) acetone-H₂O, reflux, 1 h, 2.) CH₂Cl₂, 0 deg C

6: 67 percent / NaBH₄, CeCl₃*7H₂O / ethanol; CH₂Cl₂ / -78 °C

7: 94 percent / imidazole / dimethylformamide / 40 °C

8: 80 percent / KOH / ethanol / 0.33 h / Ambient temperature; pH=10

With pyridine; 1H-imidazole; potassium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; cerium(III) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; barium carbonate; sodium iodide; mercury dichloride; In tetrachloromethane; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;
DOI:10.1246/cl.1994.37