(2R,3S,4S,5R,6S)-dimethyl [3,4,5-tris-benzyloxy-6-(t-butyldiphenylsilanyloxymethyl)-piperidin-2-yl]-methylenephosphonate

Base Information

Chemical Name:(2R,3S,4S,5R,6S)-dimethyl [3,4,5-tris-benzyloxy-6-(t-butyldiphenylsilanyloxymethyl)-piperidin-2-yl]-methylenephosphonate
CAS No.:908836-26-0
Molecular Formula:C₄₆H₅₆NO₇PSi
Molecular Weight:794.012
Hs Code.:

Synonyms:

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Chemical Property of (2R,3S,4S,5R,6S)-dimethyl [3,4,5-tris-benzyloxy-6-(t-butyldiphenylsilanyloxymethyl)-piperidin-2-yl]-methylenephosphonate

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Technology Process of (2R,3S,4S,5R,6S)-dimethyl [3,4,5-tris-benzyloxy-6-(t-butyldiphenylsilanyloxymethyl)-piperidin-2-yl]-methylenephosphonate

There total 10 articles about (2R,3S,4S,5R,6S)-dimethyl [3,4,5-tris-benzyloxy-6-(t-butyldiphenylsilanyloxymethyl)-piperidin-2-yl]-methylenephosphonate 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:

: 908836-25-9
(2S,3R,4S,5R,6S)-dimethyl 6-amino-3,4,5-tris-benzyloxy-7-t-butyldiphenylsilanyloxy-2-hydroxy-heptylphosphonate

: 908836-26-0
(2R,3S,4S,5R,6S)-dimethyl [3,4,5-tris-benzyloxy-6-(t-butyldiphenylsilanyloxymethyl)-piperidin-2-yl]-methylenephosphonate

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 18h;
DOI:10.1080/07328300600731990

Reference yield:

: 187103-77-1
2,3,4-tri-O-benzyl-D-glucitol

: 908836-26-0
(2R,3S,4S,5R,6S)-dimethyl [3,4,5-tris-benzyloxy-6-(t-butyldiphenylsilanyloxymethyl)-piperidin-2-yl]-methylenephosphonate

Guidance literature:: Multi-step reaction with 10 steps

1.1: 3.48 g / camphor-10-sulfonic acid / acetonitrile / 1 h

2.1: 96 percent / pyridine; DMAP / CH₂Cl₂ / 1 h / 20 °C

3.1: 96 percent / CSA / acetonitrile / 0.33 h / 60 °C

4.1: 95 percent / imidazole / CH₂Cl₂ / 20 °C

5.1: 71 percent / PPh₃; DIAD; diphenyl phosphoryl azide / tetrahydrofuran / 20 °C

6.1: 91 percent / Na; MeOH / 0.5 h / 20 °C

7.1: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

8.1: BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

8.2: 597 mg / tetrahydrofuran; hexane / 1 h / -78 °C

9.1: 51 percent / PPh₃ / tetrahydrofuran; H₂O / 18 h / 60 °C

10.1: PPh₃; DIAD / tetrahydrofuran / 18 h / 20 °C

With pyridine; 1H-imidazole; methanol; dmap; n-butyllithium; di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; camphor-10-sulfonic acid; sodium; Dess-Martin periodane; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; water; acetonitrile; 5.1: Mitsunobu reaction / 10.1: Mitsunobu reaction;
DOI:10.1080/07328300600731990

Reference yield:

: 908836-17-9
(2S,3R,4R)-2,3,4-tris(benzyloxy)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)butan-1-ol

: 908836-26-0
(2R,3S,4S,5R,6S)-dimethyl [3,4,5-tris-benzyloxy-6-(t-butyldiphenylsilanyloxymethyl)-piperidin-2-yl]-methylenephosphonate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 96 percent / pyridine; DMAP / CH₂Cl₂ / 1 h / 20 °C

2.1: 96 percent / CSA / acetonitrile / 0.33 h / 60 °C

3.1: 95 percent / imidazole / CH₂Cl₂ / 20 °C

4.1: 71 percent / PPh₃; DIAD; diphenyl phosphoryl azide / tetrahydrofuran / 20 °C

5.1: 91 percent / Na; MeOH / 0.5 h / 20 °C

6.1: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

7.1: BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

7.2: 597 mg / tetrahydrofuran; hexane / 1 h / -78 °C

8.1: 51 percent / PPh₃ / tetrahydrofuran; H₂O / 18 h / 60 °C

9.1: PPh₃; DIAD / tetrahydrofuran / 18 h / 20 °C

With pyridine; 1H-imidazole; methanol; dmap; n-butyllithium; di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; camphor-10-sulfonic acid; sodium; Dess-Martin periodane; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; water; acetonitrile; 4.1: Mitsunobu reaction / 9.1: Mitsunobu reaction;
DOI:10.1080/07328300600731990