(2S,3S,4R,5R)-2-C-(tert-butyldiphenylsilanyloxymethyl)-2,3:5,6-di-O-isopropylidene-D-mannofuranose

Base Information

Chemical Name:(2S,3S,4R,5R)-2-C-(tert-butyldiphenylsilanyloxymethyl)-2,3:5,6-di-O-isopropylidene-D-mannofuranose
CAS No.:870862-47-8
Molecular Formula:C₂₉H₄₀O₇Si
Molecular Weight:528.718
Hs Code.:

Synonyms:(2S,3S,4R,5R)-2-C-(tert-butyldiphenylsilanyloxymethyl)-2,3:5,6-di-O-isopropylidene-D-mannofuranose

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Chemical Property of (2S,3S,4R,5R)-2-C-(tert-butyldiphenylsilanyloxymethyl)-2,3:5,6-di-O-isopropylidene-D-mannofuranose

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Technology Process of (2S,3S,4R,5R)-2-C-(tert-butyldiphenylsilanyloxymethyl)-2,3:5,6-di-O-isopropylidene-D-mannofuranose

There total 1 articles about (2S,3S,4R,5R)-2-C-(tert-butyldiphenylsilanyloxymethyl)-2,3:5,6-di-O-isopropylidene-D-mannofuranose 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: 85.0%

: 91738-34-0
2-C-(hydroxymethyl)-2,3:5,6-di-O-isopropylidene-α-D-mannofuranose

: 58479-61-1
tert-butylchlorodiphenylsilane

: 870862-47-8
(2S,3S,4R,5R)-2-C-(tert-butyldiphenylsilanyloxymethyl)-2,3:5,6-di-O-isopropylidene-D-mannofuranose

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 21.5h;
DOI:10.1021/jo051686m

Reference yield: 97.0%

: 870862-47-8
(2S,3S,4R,5R)-2-C-(tert-butyldiphenylsilanyloxymethyl)-2,3:5,6-di-O-isopropylidene-D-mannofuranose

: 1779-49-3
Methyltriphenylphosphonium bromide

: 870862-48-9
(2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-1,2:4,5-di-O-isopropylidenedioxy-6-hepten-3-ol

Guidance literature:: Methyltriphenylphosphonium bromide; With potassium tert-butylate; In toluene; at 105 ℃; for 1h;

(2S,3S,4R,5R)-2-C-(tert-butyldiphenylsilanyloxymethyl)-2,3:5,6-di-O-isopropylidene-D-mannofuranose; In toluene; at 105 ℃; for 2h;
DOI:10.1021/jo051686m

Reference yield:

: 870862-47-8
(2S,3S,4R,5R)-2-C-(tert-butyldiphenylsilanyloxymethyl)-2,3:5,6-di-O-isopropylidene-D-mannofuranose

: 870862-59-2
(1S,2S,3R,4R)-1-hydroxymethyl-3-methoxycyclohexan-1,2,4-triol

Guidance literature:: Multi-step reaction with 8 steps

1.1: potassium tert-butoxide / toluene / 1 h / 105 °C

1.2: 97 percent / toluene / 2 h / 105 °C

2.1: 97 percent / NaH / various solvent(s); tetrahydrofuran / 4 h / 0 °C

3.1: 72 percent / acetic acid / H₂O / 4.5 h / 50 °C

4.1: NaIO₄ / tetrahydrofuran; H₂O / 1.5 h / 20 °C

5.1: 3.04 g / tetrahydrofuran / 2 h / -20 °C

6.1: 84 percent / Grubbs' second generation catalyst / toluene / 1.5 h / 80 °C

7.1: 95 percent / H₂ / Pd/C / ethyl acetate / 21 h / 20 °C

8.1: 97 percent / HCl / methanol / 120 h / 0 - 20 °C

With hydrogenchloride; sodium periodate; potassium tert-butylate; hydrogen; sodium hydride; acetic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal; In tetrahydrofuran; methanol; water; ethyl acetate; toluene; 1.2: Wittig reaction;
DOI:10.1021/jo051686m