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

Base Information

Chemical Name:N-((3S,4R,5R,6R)-4,5,7-tris(benzyloxy)-6-hydroxyhept-1-en-3-yl)acetamide
CAS No.:677334-81-5
Molecular Formula:C₃₀H₃₅NO₅
Molecular Weight:489.612
Hs Code.:

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

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Chemical Property of N-((3S,4R,5R,6R)-4,5,7-tris(benzyloxy)-6-hydroxyhept-1-en-3-yl)acetamide

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Technology Process of N-((3S,4R,5R,6R)-4,5,7-tris(benzyloxy)-6-hydroxyhept-1-en-3-yl)acetamide

There total 4 articles about N-((3S,4R,5R,6R)-4,5,7-tris(benzyloxy)-6-hydroxyhept-1-en-3-yl)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: 60.0%

: 1779-49-3
Methyltriphenylphosphonium bromide

: 121123-45-3
3,4,6-tri-O-benzyl-2-acetamido-2-deoxyamino-α-D-glucopyranose

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

Guidance literature:: Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 1.08333h; Inert atmosphere;

3,4,6-tri-O-benzyl-2-acetamido-2-deoxyamino-α-D-glucopyranose; In tetrahydrofuran; hexane; at 0 ℃; for 13h; Inert atmosphere; Reflux;
DOI:10.1021/jo501340s

Reference yield: 49.0%

: 677334-79-1
N-(4-methoxy-benzyl)-N-[1-(1,2,4-tris-benzyloxy-3-hydroxy-butyl)-allyl]-acetamide

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

Guidance literature:: With ammonium cerium(IV) nitrate; In methanol;
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

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

Guidance literature:: Multi-step reaction with 3 steps

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

2.1: CH₂Cl₂

2.2: 50 percent / K₂CO₃ / methanol

3.1: 49 percent / CAN / methanol

With ammonium cerium(IV) nitrate; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/j.tetlet.2003.12.135