Phenyl-carbamic acid (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Phenyl-carbamic acid (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester
• CAS No.: 115533-40-9
• Molecular Formula: C₄₃H₄₆N₂O₁₂S
• Molecular Weight: 814.91

Synonyms:Phenyl-carbamic acid (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester

Chemical Property of Phenyl-carbamic acid (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of Phenyl-carbamic acid (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester

There total 15 articles about Phenyl-carbamic acid (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl 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: 90.0%

ethyl O-<2,4,6-tri-O-acetyl-3-O-(N-phenylcarbamoyl)-β-D-glucopyranosyl>-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (115533-34-1) → Phenyl-carbamic acid (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester (115533-40-9)

Guidance literature:

With potassium carbonate; In methanol;

Reference yield:

phenyl isocyanate (103-71-9) → Phenyl-carbamic acid (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester (115533-40-9)

Guidance literature:

Multi-step reaction with 6 steps

2: H₂SO₄ / H₂O; dioxane

3: pyridine

4: 80 percent / HBr / acetic acid

5: 82 percent / AgOTf / CH₂Cl₂ / -30 °C

6: 90 percent / K₂CO₃ / methanol

With sulfuric acid; hydrogen bromide; silver trifluoromethanesulfonate; potassium carbonate; In 1,4-dioxane; pyridine; methanol; dichloromethane; water; acetic acid;

Reference yield:

2,4,6-tri-O-acetyl-3-O-(N-phenylcarbamoyl)-α-D-glucopyranosyl bromide (115559-99-4) → Phenyl-carbamic acid (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester (115533-40-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / AgOTf / CH₂Cl₂ / -30 °C

2: 90 percent / K₂CO₃ / methanol

With silver trifluoromethanesulfonate; potassium carbonate; In methanol; dichloromethane;

upstream raw materials:

ethyl O-<2,4,6-tri-O-acetyl-3-O-(N-phenylcarbamoyl)-β-D-glucopyranosyl>-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

phenyl isocyanate

1,2-5,6-di-O-isopropylidene-3-O-(N-phenylcarbamoyl)-α-D-glucofuranose

2,4,6-tri-O-acetyl-3-O-(N-phenylcarbamoyl)-α-D-glucopyranosyl bromide

Downstream raw materials:

ethyl O-<4,6-O-benzylidene-3-O-(N-phenylcarbamoyl)-β-D-glucopyranosyl>-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Phenyl-carbamic acid (2R,4aR,6S,7R,8R,8aR)-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-5-((3aS,4S,5aR,8R,9aR,9bS)-2-oxo-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

2-((2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-5-{(3aS,4S,5aR,8R,9aR,9bS)-8-phenyl-2-[(Z)-phenylimino]-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yloxy}-tetrahydro-pyran-3-yl)-isoindole-1,3-dione

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