(2R,3S,4S,6R)-2,3-benzyloxy-4-(tert-butyldiphenylsilanyloxymethyl)-6-methoxymethyloxy-cyclohexanone

Base Information

Chemical Name:(2R,3S,4S,6R)-2,3-benzyloxy-4-(tert-butyldiphenylsilanyloxymethyl)-6-methoxymethyloxy-cyclohexanone
CAS No.:867258-53-5
Molecular Formula:C₃₉H₄₆O₆Si
Molecular Weight:638.876
Hs Code.:

Synonyms:(2R,3S,4S,6R)-2,3-benzyloxy-4-(tert-butyldiphenylsilanyloxymethyl)-6-methoxymethyloxy-cyclohexanone

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Chemical Property of (2R,3S,4S,6R)-2,3-benzyloxy-4-(tert-butyldiphenylsilanyloxymethyl)-6-methoxymethyloxy-cyclohexanone

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Technology Process of (2R,3S,4S,6R)-2,3-benzyloxy-4-(tert-butyldiphenylsilanyloxymethyl)-6-methoxymethyloxy-cyclohexanone

There total 9 articles about (2R,3S,4S,6R)-2,3-benzyloxy-4-(tert-butyldiphenylsilanyloxymethyl)-6-methoxymethyloxy-cyclohexanone 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: 89.0%

: 867258-56-8
3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-1-O-methoxymethyl-5a-carba-α-D-altropyranose

: 867258-53-5
(2R,3S,4S,6R)-2,3-benzyloxy-4-(tert-butyldiphenylsilanyloxymethyl)-6-methoxymethyloxy-cyclohexanone

Guidance literature:: With 4 A molecular sieve; pyridinium chlorochromate; In dichloromethane; for 11h; Heating;
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

: 867258-53-5
(2R,3S,4S,6R)-2,3-benzyloxy-4-(tert-butyldiphenylsilanyloxymethyl)-6-methoxymethyloxy-cyclohexanone

Guidance literature:: Multi-step reaction with 6 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

4.1: 84 percent / (i-Pr)2NEt / CH₂Cl₂ / 15 h / Heating

5.1: 93.6 percent / NaOMe / methanol / 14 h / 20 °C

6.1: 89 percent / molecular sieves 4 Angstroem; pyridinium chlorochromate / CH₂Cl₂ / 11 h / Heating

With sodium tetrahydroborate; 4 A molecular sieve; sodium methylate; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In methanol; dichloromethane;
DOI:10.1016/j.tetasy.2005.07.010

Reference yield:

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

: 867258-53-5
(2R,3S,4S,6R)-2,3-benzyloxy-4-(tert-butyldiphenylsilanyloxymethyl)-6-methoxymethyloxy-cyclohexanone

Guidance literature:: Multi-step reaction with 3 steps

1: 84 percent / (i-Pr)2NEt / CH₂Cl₂ / 15 h / Heating

2: 93.6 percent / NaOMe / methanol / 14 h / 20 °C

3: 89 percent / molecular sieves 4 Angstroem; pyridinium chlorochromate / CH₂Cl₂ / 11 h / Heating

With 4 A molecular sieve; sodium methylate; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In methanol; dichloromethane;
DOI:10.1016/j.tetasy.2005.07.010