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

Base Information

Chemical Name:1,2-anhydro-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-β-D-mannopyranose
CAS No.:867258-60-4
Molecular Formula:C₃₇H₄₂O₄Si
Molecular Weight:578.824
Hs Code.:

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

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

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

There total 6 articles about 1,2-anhydro-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-β-D-mannopyranose 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: 84.7%

: 867258-57-9
3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-β-D-mannopyranose

: 867258-60-4
1,2-anhydro-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-β-D-mannopyranose

Guidance literature:: 3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-β-D-mannopyranose; With Trimethyl orthoacetate; pyridinium p-toluenesulfonate; triethylamine; In dichloromethane; at 20 ℃; for 0.666667h;

With Acetyl bromide; triethylamine; In dichloromethane; at 20 ℃; for 4h;

With sodium methylate; In methanol; at 20 ℃; for 0.5h;
DOI:10.1016/j.tetasy.2005.07.010

Reference yield:

: 867258-59-1
(1R,2R,3R)-1,2-di-benzyloxy-3-(tert-butyldiphenyl-silanyloxymethyl)-cyclohex-5-ene

: 867258-61-5
1,2-anhydro-3,4-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-α-D-glucopyranose

: 867258-60-4
1,2-anhydro-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-β-D-mannopyranose

Guidance literature:: (1R,2R,3R)-1,2-di-benzyloxy-3-(tert-butyldiphenyl-silanyloxymethyl)-cyclohex-5-ene; With hydrogenchloride; N-iodo-succinimide; In 1,4-dioxane; at 20 ℃;

With sodium methylate; In methanol; at 20 ℃; for 6h;
DOI:10.1016/j.tetasy.2005.07.010

Reference yield:

: 867258-65-9
3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-1,2-di-O-(methoxymethyl)-5a-carba-β-D-mannopyranose

: 867258-60-4
1,2-anhydro-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-β-D-mannopyranose

Guidance literature:: Multi-step reaction with 3 steps

1.1: 78.4 percent / molecular sieves 4 Angstroem; TMSBr / CH₂Cl₂ / 4 h / -20 °C

2.1: 90.4 percent / PPh₃; imidazole; I₂ / toluene / 3.42 h / Heating

3.1: NIS; aq. HCl / dioxane / 20 °C

3.2: 4 mg / NaOMe / methanol / 6 h / 20 °C

With 1H-imidazole; hydrogenchloride; N-iodo-succinimide; trimethylsilyl bromide; 4 A molecular sieve; iodine; triphenylphosphine; In 1,4-dioxane; dichloromethane; toluene;
DOI:10.1016/j.tetasy.2005.07.010