Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(2-hydroxy-5-nitro-benzyloxy)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(2-hydroxy-5-nitro-benzyloxy)-tetrahydro-pyran-4-yl ester
• CAS No.: 403511-54-6
• Molecular Formula: C₂₇H₂₆N₂O₁₃
• Molecular Weight: 586.509

Synonyms:Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(2-hydroxy-5-nitro-benzyloxy)-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(2-hydroxy-5-nitro-benzyloxy)-tetrahydro-pyran-4-yl ester

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Technology Process of Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(2-hydroxy-5-nitro-benzyloxy)-tetrahydro-pyran-4-yl ester

There total 1 articles about Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(2-hydroxy-5-nitro-benzyloxy)-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: 84.0%

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) + 2-hydroxy-5-nitrobenzyl alcohol (39224-61-8) → Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(2-hydroxy-5-nitro-benzyloxy)-tetrahydro-pyran-4-yl ester (403511-54-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/S0040-4039(01)01826-3

Reference yield: 85.0%

2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate (140209-88-7) + Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(2-hydroxy-5-nitro-benzyloxy)-tetrahydro-pyran-4-yl ester (403511-54-6) → C88H74N2O30

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1139/v02-156

Reference yield: 70.0%

2,3,4,6-tetra-O-benzoyl-1-O-trichloroacetimidoyl-α-D-galactopyranose (149707-75-5,149707-76-6,138479-78-4) + Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(2-hydroxy-5-nitro-benzyloxy)-tetrahydro-pyran-4-yl ester (403511-54-6) → C61H52N2O22 (403511-56-8)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1016/S0040-4039(01)01826-3

upstream raw materials:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

2-hydroxy-5-nitrobenzyl alcohol

Downstream raw materials:

C₆₁H₅₂N₂O₂₂

N-{(2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-[5-nitro-2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzyloxy]-tetrahydro-pyran-3-yl}-acetamide

(2S,3R,4S,5R,6R)-2-[2-((2R,3R,4R,5S,6R)-3-Azido-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-4-nitro-phenoxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

{(2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-[5-nitro-2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzyloxy]-tetrahydro-pyran-3-yl}-carbamic acid allyl ester

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