(3R,4R,5S)-2-[(Z)-1-benzoylamino-1-[1-hydroxymethyl-2,2-dimethoxypropyl]-carbamoyl]methylidene-3,4-dibenzyloxy-1-(prop-2-en-1-yloxy)carbonyl-5-(methanesulfonyloxy)methylpyrrolidine

Base Information

Chemical Name:(3R,4R,5S)-2-[(Z)-1-benzoylamino-1-[1-hydroxymethyl-2,2-dimethoxypropyl]-carbamoyl]methylidene-3,4-dibenzyloxy-1-(prop-2-en-1-yloxy)carbonyl-5-(methanesulfonyloxy)methylpyrrolidine
CAS No.:161275-56-5
Molecular Formula:C₃₉H₄₇N₃O₁₂S
Molecular Weight:781.881
Hs Code.:

(3R,4R,5S)-2-[(Z)-1-benzoylamino-1-[1-hydroxymethyl-2,2-dimethoxypropyl]-carbamoyl]methylidene-3,4-dibenzyloxy-1-(prop-2-en-1-yloxy)carbonyl-5-(methanesulfonyloxy)methylpyrrolidine

Synonyms:(3R,4R,5S)-2-[(Z)-1-benzoylamino-1-[1-hydroxymethyl-2,2-dimethoxypropyl]-carbamoyl]methylidene-3,4-dibenzyloxy-1-(prop-2-en-1-yloxy)carbonyl-5-(methanesulfonyloxy)methylpyrrolidine

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Chemical Property of (3R,4R,5S)-2-[(Z)-1-benzoylamino-1-[1-hydroxymethyl-2,2-dimethoxypropyl]-carbamoyl]methylidene-3,4-dibenzyloxy-1-(prop-2-en-1-yloxy)carbonyl-5-(methanesulfonyloxy)methylpyrrolidine

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Technology Process of (3R,4R,5S)-2-[(Z)-1-benzoylamino-1-[1-hydroxymethyl-2,2-dimethoxypropyl]-carbamoyl]methylidene-3,4-dibenzyloxy-1-(prop-2-en-1-yloxy)carbonyl-5-(methanesulfonyloxy)methylpyrrolidine

There total 5 articles about (3R,4R,5S)-2-[(Z)-1-benzoylamino-1-[1-hydroxymethyl-2,2-dimethoxypropyl]-carbamoyl]methylidene-3,4-dibenzyloxy-1-(prop-2-en-1-yloxy)carbonyl-5-(methanesulfonyloxy)methylpyrrolidine 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: 79.0%

: 161275-55-4
(3R,4R,5S)-2-[(Z)-1-benzoylamino-1-[1-(t-butyldiphenylsiloxy)methyl-2,2-dimethoxypropyl]-carbamoyl]methylidene-3,4-dibenzyloxy-1-(prop-2-en-1-yloxy)carbonyl-5-(methanesulfonyloxy)methylpyrrolidine

: 161275-56-5
(3R,4R,5S)-2-[(Z)-1-benzoylamino-1-[1-hydroxymethyl-2,2-dimethoxypropyl]-carbamoyl]methylidene-3,4-dibenzyloxy-1-(prop-2-en-1-yloxy)carbonyl-5-(methanesulfonyloxy)methylpyrrolidine

Guidance literature:: With pyridine hydrogenfluoride; In pyridine; at 0 - 20 ℃; for 1.5h;
DOI:10.1016/S0040-4020(03)00378-8

Reference yield:

: 161150-58-9
[1-(tert-butyldiphenylsilanyloxymethyl)-2,2-dimethoxypropyl]carbamic acid benzyl ester

: 161275-56-5
(3R,4R,5S)-2-[(Z)-1-benzoylamino-1-[1-hydroxymethyl-2,2-dimethoxypropyl]-carbamoyl]methylidene-3,4-dibenzyloxy-1-(prop-2-en-1-yloxy)carbonyl-5-(methanesulfonyloxy)methylpyrrolidine

Guidance literature:: Multi-step reaction with 3 steps

1: 93 percent / H₂ / 10 percent Pd/C / methanol / 14 h / 20 °C / 760 Torr

2: 15 percent / DMAP / toluene / 2 h / 50 °C

3: 79 percent / HF-pyridine complex / pyridine / 1.5 h / 0 - 20 °C

With dmap; hydrogen; pyridine hydrogenfluoride; palladium on activated charcoal; In pyridine; methanol; toluene;
DOI:10.1016/S0040-4020(03)00378-8

Reference yield:

: 560130-29-2
4-[(3R,4R,5S)-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidin-2-ylidene]-2-phenyl-4H-oxazol-5-one

: 161275-56-5
(3R,4R,5S)-2-[(Z)-1-benzoylamino-1-[1-hydroxymethyl-2,2-dimethoxypropyl]-carbamoyl]methylidene-3,4-dibenzyloxy-1-(prop-2-en-1-yloxy)carbonyl-5-(methanesulfonyloxy)methylpyrrolidine

Guidance literature:: Multi-step reaction with 3 steps

1: 27 percent / DMAP / tetrahydrofuran / 0.17 h / 20 °C

2: 15 percent / DMAP / toluene / 2 h / 50 °C

3: 79 percent / HF-pyridine complex / pyridine / 1.5 h / 0 - 20 °C

With dmap; pyridine hydrogenfluoride; In tetrahydrofuran; pyridine; toluene;
DOI:10.1016/S0040-4020(03)00378-8