5-(N-(benzyloxycarbonyl)sarcosinamido)-5-hydroxymethyl-2-phenyl-1,3-dioxane

Base Information

• Chemical Name: 5-(N-(benzyloxycarbonyl)sarcosinamido)-5-hydroxymethyl-2-phenyl-1,3-dioxane
• CAS No.: 159945-08-1
• Molecular Formula: C₂₁H₂₄N₂O₆
• Molecular Weight: 400.431

Synonyms:5-(N-(benzyloxycarbonyl)sarcosinamido)-5-hydroxymethyl-2-phenyl-1,3-dioxane

Chemical Property of 5-(N-(benzyloxycarbonyl)sarcosinamido)-5-hydroxymethyl-2-phenyl-1,3-dioxane

Chemical Property:

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Technology Process of 5-(N-(benzyloxycarbonyl)sarcosinamido)-5-hydroxymethyl-2-phenyl-1,3-dioxane

There total 2 articles about 5-(N-(benzyloxycarbonyl)sarcosinamido)-5-hydroxymethyl-2-phenyl-1,3-dioxane 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: 47.0%

benzaldehyde (100-52-7) + N-<2-hydroxy-1,1-bis(hydroxymethyl)ethyl>-Nα-(benzyloxycarbonyl)glycinamide (91202-74-3) → 5-(N-(benzyloxycarbonyl)sarcosinamido)-5-hydroxymethyl-2-phenyl-1,3-dioxane (159945-08-1)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; at 20 ℃; for 0.166667h;

DOI:10.1016/S0040-4039(00)76654-8

Reference yield:

N-(Benzyloxycarbonyl)glycine (1138-80-3) → 5-(N-(benzyloxycarbonyl)sarcosinamido)-5-hydroxymethyl-2-phenyl-1,3-dioxane (159945-08-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / N-ethoxy-1-ethoxy dihydroquinoleine / ethanol / 6 h / Heating

2: p-toluenesulfonic acid / acetonitrile / 24 h

With N-ethoxy-1-ethoxy dihydroquinoleine; toluene-4-sulfonic acid; In ethanol; acetonitrile;

DOI:10.1016/0009-3084(95)02475-X

Reference yield: 90.0%

5-(N-(benzyloxycarbonyl)sarcosinamido)-5-hydroxymethyl-2-phenyl-1,3-dioxane (159945-08-1) + 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → Acetic acid (2S,3R,4R,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[5-(2-benzyloxycarbonylamino-acetylamino)-2-phenyl-[1,3]dioxan-5-ylmethoxy]-tetrahydro-pyran-4-yl ester

Guidance literature:

With mercury(II) cyanide; In acetonitrile; ultrasonication;

DOI:10.1016/S0040-4039(00)76654-8

upstream raw materials:

benzaldehyde

N-<2-hydroxy-1,1-bis(hydroxymethyl)ethyl>-N^α-(benzyloxycarbonyl)glycinamide

N-(Benzyloxycarbonyl)glycine

Downstream raw materials:

5-(O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)hydroxymethyl)-5-(N-(benzyloxycarbonyl)glycinamido)-2-phenyl-1,3-dioxane

Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[5-(2-amino-acetylamino)-2-phenyl-[1,3]dioxan-5-ylmethoxy]-tetrahydro-pyran-4-yl ester

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