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

Base Information

Chemical Name:N-[(1S,2R,3S,4R)-2,3,5-Tris-benzyloxy-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methoxymethoxy-pentyl]-acetamide
CAS No.:677334-83-7
Molecular Formula:C₃₅H₄₅NO₈
Molecular Weight:607.744
Hs Code.:

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

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

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

There total 5 articles about N-[(1S,2R,3S,4R)-2,3,5-Tris-benzyloxy-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methoxymethoxy-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: 94.0%

: 107-30-2
chloromethyl methyl ether

: 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

: 677334-83-7
N-[(1S,2R,3S,4R)-2,3,5-Tris-benzyloxy-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methoxymethoxy-pentyl]-acetamide

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane;
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

: 677334-83-7
N-[(1S,2R,3S,4R)-2,3,5-Tris-benzyloxy-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methoxymethoxy-pentyl]-acetamide

Guidance literature:: Multi-step reaction with 6 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

6.1: 94 percent / (i-Pr)2NEt / CH₂Cl₂

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

Reference yield:

: 677334-81-5
N-((3S,4R,5R,6R)-4,5,7-tris(benzyloxy)-6-hydroxyhept-1-en-3-yl)acetamide

: 677334-83-7
N-[(1S,2R,3S,4R)-2,3,5-Tris-benzyloxy-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methoxymethoxy-pentyl]-acetamide

Guidance literature:: Multi-step reaction with 3 steps

1: 99 percent / OsO₄; NMO / acetone; H₂O

2: 90 percent / p-TsOH / acetone

3: 94 percent / (i-Pr)2NEt / CH₂Cl₂

With osmium(VIII) oxide; N-methyl-2-indolinone; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In dichloromethane; water; acetone;
DOI:10.1016/j.tetlet.2003.12.135