N-[(1S,2R,3R,4R)-2,3,5-Tris-benzyloxy-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-pentyl]-acetamide

Base Information

Chemical Name:N-[(1S,2R,3R,4R)-2,3,5-Tris-benzyloxy-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-pentyl]-acetamide
CAS No.:677334-89-3
Molecular Formula:C₃₃H₄₁NO₇
Molecular Weight:563.691
Hs Code.:

Synonyms:N-[(1S,2R,3R,4R)-2,3,5-Tris-benzyloxy-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-pentyl]-acetamide

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Chemical Property of N-[(1S,2R,3R,4R)-2,3,5-Tris-benzyloxy-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-pentyl]-acetamide

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Technology Process of N-[(1S,2R,3R,4R)-2,3,5-Tris-benzyloxy-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-pentyl]-acetamide

There total 5 articles about N-[(1S,2R,3R,4R)-2,3,5-Tris-benzyloxy-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-pentyl]-acetamide 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: 90.0%

: 77-76-9
2,2-dimethoxy-propane

: 677334-92-8
N-[(1S,2R,3R,4R)-2,3,5-Tris-benzyloxy-1-(1,2-dihydroxy-ethyl)-4-hydroxy-pentyl]-acetamide

: 677334-89-3
N-[(1S,2R,3R,4R)-2,3,5-Tris-benzyloxy-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-pentyl]-acetamide

Guidance literature:: With toluene-4-sulfonic acid; In acetone;
DOI:10.1016/j.tetlet.2003.12.135

Reference yield:

: 157831-24-8
((3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-(4-methoxy-benzyl)-amine

: 677334-89-3
N-[(1S,2R,3R,4R)-2,3,5-Tris-benzyloxy-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-pentyl]-acetamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: 62 percent / tetrahydrofuran / -78 - -40 °C

2.1: CH₂Cl₂

2.2: 50 percent / K₂CO₃ / methanol

3.1: 49 percent / CAN / methanol

4.1: 99 percent / OsO₄; NMO / acetone; H₂O

5.1: 90 percent / p-TsOH / acetone

With osmium(VIII) oxide; N-methyl-2-indolinone; ammonium cerium(IV) nitrate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; water; acetone;
DOI:10.1016/j.tetlet.2003.12.135

Reference yield:

: 157831-25-9
(2R,3R,4R,5S)-1,3,4-Tris-benzyloxy-5-(4-methoxy-benzylamino)-hept-6-en-2-ol

: 677334-89-3
N-[(1S,2R,3R,4R)-2,3,5-Tris-benzyloxy-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-pentyl]-acetamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: CH₂Cl₂

1.2: 50 percent / K₂CO₃ / methanol

2.1: 49 percent / CAN / methanol

3.1: 99 percent / OsO₄; NMO / acetone; H₂O

4.1: 90 percent / p-TsOH / acetone

With osmium(VIII) oxide; N-methyl-2-indolinone; ammonium cerium(IV) nitrate; toluene-4-sulfonic acid; In methanol; dichloromethane; water; acetone;
DOI:10.1016/j.tetlet.2003.12.135