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

Base Information

• Chemical Name: {3-[(2R,3R,4S,5R)-4-((2R,3R,4S,5S,6R)-3-Benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-5-benzyloxymethyl-3-hydroxy-tetrahydro-furan-2-yloxy]-propyl}-carbamic acid benzyl ester
• CAS No.: 305839-29-6
• Molecular Formula: C₄₃H₅₁NO₁₂
• Molecular Weight: 773.877

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of {3-[(2R,3R,4S,5R)-4-((2R,3R,4S,5S,6R)-3-Benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-5-benzyloxymethyl-3-hydroxy-tetrahydro-furan-2-yloxy]-propyl}-carbamic acid benzyl ester

There total 8 articles about {3-[(2R,3R,4S,5R)-4-((2R,3R,4S,5S,6R)-3-Benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-5-benzyloxymethyl-3-hydroxy-tetrahydro-furan-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:

1-((3-benzyloxycarbonylamino)-propyl)-2-O-acetyl-5-O-benzyl-3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-β-D-ribofuranoside (305839-25-2) → {3-[(2R,3R,4S,5R)-4-((2R,3R,4S,5S,6R)-3-Benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-5-benzyloxymethyl-3-hydroxy-tetrahydro-furan-2-yloxy]-propyl}-carbamic acid benzyl ester (305839-29-6)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 1.5h;

DOI:10.1002/1099-0690(200009)2000:17<3085::AID-EJOC3085>3.0.CO;2-A

Reference yield:

5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose (2592-42-9,23202-83-7) → {3-[(2R,3R,4S,5R)-4-((2R,3R,4S,5S,6R)-3-Benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-5-benzyloxymethyl-3-hydroxy-tetrahydro-furan-2-yloxy]-propyl}-carbamic acid benzyl ester (305839-29-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / NIS; molecular sieves 4 Angstroem / TMSOTf / toluene; dioxane / 0.25 h / 20 °C

2: AcOH / H₂O; ethane-1,2-diol / 1 h / Heating

3: pyridine / 4 h / 20 °C

4: 92 percent / SnCl₄; molecular sieves 4 Angstroem / 1,2-dichloro-ethane / 16 h / 20 °C

5: NaOMe / methanol / 1.5 h / 20 °C

With N-iodo-succinimide; 4 A molecular sieve; sodium methylate; tin(IV) chloride; acetic acid; trimethylsilyl trifluoromethanesulfonate; In 1,4-dioxane; pyridine; methanol; water; ethylene glycol; 1,2-dichloro-ethane; toluene; 1: Glycosylation / 2: Hydrolysis / 3: Acetylation / 4: Glycosylation / 5: Deacetylation;

DOI:10.1002/1099-0690(200009)2000:17<3085::AID-EJOC3085>3.0.CO;2-A

Reference yield:

(2'S,3'S)-ethyl 2,6-di-O-benzyl-3,4-di-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-β-D-glucopyranoside (197644-80-7) → {3-[(2R,3R,4S,5R)-4-((2R,3R,4S,5S,6R)-3-Benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-5-benzyloxymethyl-3-hydroxy-tetrahydro-furan-2-yloxy]-propyl}-carbamic acid benzyl ester (305839-29-6)

Guidance literature:

Multi-step reaction with 7 steps

1: AcOH / H₂O / 1 h / Heating

2: pyridine / 0.5 h / 20 °C

3: 89 percent / NIS; molecular sieves 4 Angstroem / TMSOTf / toluene; dioxane / 0.25 h / 20 °C

4: AcOH / H₂O; ethane-1,2-diol / 1 h / Heating

5: pyridine / 4 h / 20 °C

6: 92 percent / SnCl₄; molecular sieves 4 Angstroem / 1,2-dichloro-ethane / 16 h / 20 °C

7: NaOMe / methanol / 1.5 h / 20 °C

With N-iodo-succinimide; 4 A molecular sieve; sodium methylate; tin(IV) chloride; acetic acid; trimethylsilyl trifluoromethanesulfonate; In 1,4-dioxane; pyridine; methanol; water; ethylene glycol; 1,2-dichloro-ethane; toluene; 1: Hydrolysis / 2: Acetylation / 3: Glycosylation / 4: Hydrolysis / 5: Acetylation / 6: Glycosylation / 7: Deacetylation;

DOI:10.1002/1099-0690(200009)2000:17<3085::AID-EJOC3085>3.0.CO;2-A

upstream raw materials:

1-((3-benzyloxycarbonylamino)-propyl)-2-O-acetyl-5-O-benzyl-3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-β-D-ribofuranoside

5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose

1,2-di-O-acetyl-3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-5-O-benzyl-α/β-D-ribofuranoside

(2'S,3'S)-ethyl 2,6-di-O-benzyl-3,4-di-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-β-D-glucopyranoside

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