2-O-benzoyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-α-D-altropyranose

Base Information

Chemical Name:2-O-benzoyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-α-D-altropyranose
CAS No.:867258-54-6
Molecular Formula:C₄₄H₄₈O₆Si
Molecular Weight:700.947
Hs Code.:

Synonyms:2-O-benzoyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-α-D-altropyranose

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Chemical Property of 2-O-benzoyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-α-D-altropyranose

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Technology Process of 2-O-benzoyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-α-D-altropyranose

There total 6 articles about 2-O-benzoyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-α-D-altropyranose 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: 68.6%

: 867258-51-3
(2S,3R,4R,5S)-2-benzoyloxy-5-(tert-butyldiphenylsilanyloxymethyl)-3,4-di-benzyloxy-cyclohexanone

: 867258-54-6
2-O-benzoyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-α-D-altropyranose

: 867258-48-8
2-O-benzoyl-3,4-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-β-D-altropyranose

Guidance literature:: With sodium tetrahydroborate; In methanol; dichloromethane; at -10 ℃; for 1.83333h;
DOI:10.1016/j.tetasy.2005.07.010

Reference yield:

: 867258-45-5
3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-β-D-altropyranose

: 867258-54-6
2-O-benzoyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-α-D-altropyranose

Guidance literature:: Multi-step reaction with 3 steps

1.1: TSA / CH₂Cl₂ / 0.5 h / 20 °C

1.2: 52.5 percent / aq. AcOH / 0.17 h / 20 °C

2.1: 93.7 percent / molecular sieves 4 Angstroem; pyridinium chlorochromate / CH₂Cl₂ / 4 h / Heating

3.1: 68.6 percent / NaBH₄ / CH₂Cl₂; methanol / 1.83 h / -10 °C

With sodium tetrahydroborate; 4 A molecular sieve; pyridinium chlorochromate; In methanol; dichloromethane;
DOI:10.1016/j.tetasy.2005.07.010

Reference yield:

: 867258-44-4
3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-1,2-di-O-(methoxymethyl)-5a-carba-β-D-altropyranose

: 867258-54-6
2-O-benzoyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-α-D-altropyranose

Guidance literature:: Multi-step reaction with 4 steps

1.1: 64 percent / molecular sieves 4 Angstroem; TMSBr / CH₂Cl₂ / 0.67 h / -20 °C

2.1: TSA / CH₂Cl₂ / 0.5 h / 20 °C

2.2: 52.5 percent / aq. AcOH / 0.17 h / 20 °C

3.1: 93.7 percent / molecular sieves 4 Angstroem; pyridinium chlorochromate / CH₂Cl₂ / 4 h / Heating

4.1: 68.6 percent / NaBH₄ / CH₂Cl₂; methanol / 1.83 h / -10 °C

With sodium tetrahydroborate; trimethylsilyl bromide; 4 A molecular sieve; pyridinium chlorochromate; In methanol; dichloromethane;
DOI:10.1016/j.tetasy.2005.07.010