{3-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-propyl}-carbamic acid benzyl ester

Base Information

• Chemical Name: {3-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-propyl}-carbamic acid benzyl ester
• CAS No.: 809232-05-1
• Molecular Formula: C₂₆H₃₉NO₁₃
• Molecular Weight: 573.595

Synonyms:{3-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-propyl}-carbamic acid benzyl ester

Chemical Property of {3-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-propyl}-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of {3-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-propyl}-carbamic acid benzyl ester

There total 3 articles about {3-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-propyl}-carbamic acid benzyl ester 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:

allyl bromide (106-95-6) + 3-(benzyloxycarbonylamino)propyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (726134-69-6) → {3-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-propyl}-carbamic acid benzyl ester (809232-05-1)

Guidance literature:

3-(benzyloxycarbonylamino)propyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside; With sodium methylate; In methanol; at 20 ℃; for 5h;

With di(n-butyl)tin oxide; In methanol; for 16h; Heating;

allyl bromide; With tetra-(n-butyl)ammonium iodide; In benzene; for 5h; Heating;

DOI:10.1021/ol0483246

Reference yield:

lactose octaacetate (3616-19-1,5328-50-7,5346-90-7,6291-42-5,6920-00-9,20764-63-0,20880-60-8,20880-65-3,22352-19-8,23973-20-8,32447-69-1,34213-32-6,53956-64-2,56907-29-0,56994-12-8,56994-13-9,57128-38-8,67650-36-6,68036-17-9,68036-19-1,78215-50-6,78215-51-7,79549-48-7,80446-82-8,85249-04-3,93221-83-1,93779-27-2,111407-83-1,111407-84-2,111407-85-3,120328-65-6,123809-59-6,132341-46-9,132341-47-0,132341-49-2,145307-94-4,52554-32-2) → {3-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-propyl}-carbamic acid benzyl ester (809232-05-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 43 percent / BF₃*Et₂O / CH₂Cl₂ / 20 °C

2.1: NaOMe / methanol / 20 °C

2.2: Bu₂SnO / methanol / 110 °C

2.3: Bu₄NI; molecular sieves 4 Angstroem / benzene / 120 °C

With boron trifluoride diethyl etherate; sodium methylate; In methanol; dichloromethane;

DOI:10.1016/j.tet.2005.02.023

Reference yield:

3-[(N-benzyloxycarbonyl)amino]propanol (34637-22-4) → {3-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-propyl}-carbamic acid benzyl ester (809232-05-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 43 percent / BF₃*Et₂O / CH₂Cl₂ / 20 °C

2.1: NaOMe / methanol / 20 °C

2.2: Bu₂SnO / methanol / 110 °C

2.3: Bu₄NI; molecular sieves 4 Angstroem / benzene / 120 °C

With boron trifluoride diethyl etherate; sodium methylate; In methanol; dichloromethane;

DOI:10.1016/j.tet.2005.02.023

upstream raw materials:

allyl bromide

3-(benzyloxycarbonylamino)propyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

lactose octaacetate

3-[(N-benzyloxycarbonyl)amino]propanol

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