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

Base Information

Chemical Name:3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-1,2-di-O-(methoxymethyl)-5a-carba-β-D-altropyranose
CAS No.:867258-44-4
Molecular Formula:C₄₁H₅₂O₇Si
Molecular Weight:684.945
Hs Code.:

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

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Chemical Property of 3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-1,2-di-O-(methoxymethyl)-5a-carba-β-D-altropyranose

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Technology Process of 3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-1,2-di-O-(methoxymethyl)-5a-carba-β-D-altropyranose

There total 1 articles about 3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-1,2-di-O-(methoxymethyl)-5a-carba-β-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: 90.2%

: 100-39-0
benzyl bromide

: 677745-86-7
(1R,2R,3S,4R,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3,4-bis-methoxymethoxy-cyclohexane-1,2-diol

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

Guidance literature:: (1R,2R,3S,4R,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3,4-bis-methoxymethoxy-cyclohexane-1,2-diol; With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 20 ℃; for 48h;
DOI:10.1016/j.tetasy.2005.07.010

Reference yield: 64.0%

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

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

Guidance literature:: With trimethylsilyl bromide; 4 A molecular sieve; In dichloromethane; at -20 ℃; for 0.666667h;
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

: 867258-50-2
(2R,4S,5R,6R)-2-benzoyloxy-4-(tert-butyldiphenylsilanyloxymethyl)-5,6-dibenzyloxycyclohexanone

Guidance literature:: Multi-step reaction with 3 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: 39.6 percent / aq. AcOH / 0.17 h / 20 °C

3.1: 99.6 percent / molecular sieves 4 Angstroem; pyridinium chlorochromate / CH₂Cl₂ / 5 h / 20 °C

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