N-{(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-hydroxy-2-[((E)-propenyl)oxy]-tetrahydro-pyran-3-yl}-phthalamic acid

Base Information

• Chemical Name: N-{(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-hydroxy-2-[((E)-propenyl)oxy]-tetrahydro-pyran-3-yl}-phthalamic acid
• CAS No.: 82185-86-2
• Molecular Formula: C₃₁H₃₃NO₈
• Molecular Weight: 547.605

Synonyms:N-{(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-hydroxy-2-[((E)-propenyl)oxy]-tetrahydro-pyran-3-yl}-phthalamic acid

Chemical Property of N-{(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-hydroxy-2-[((E)-propenyl)oxy]-tetrahydro-pyran-3-yl}-phthalamic acid

Chemical Property:

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Technology Process of N-{(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-hydroxy-2-[((E)-propenyl)oxy]-tetrahydro-pyran-3-yl}-phthalamic acid

There total 2 articles about N-{(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-hydroxy-2-[((E)-propenyl)oxy]-tetrahydro-pyran-3-yl}-phthalamic acid 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: 100.0%

phthalic anhydride (85-44-9) + (2R,3S,4R,5R,6S)-5-Amino-4-benzyloxy-2-benzyloxymethyl-6-[((E)-propenyl)oxy]-tetrahydro-pyran-3-ol (82185-85-1) → N-{(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-hydroxy-2-[((E)-propenyl)oxy]-tetrahydro-pyran-3-yl}-phthalamic acid (82185-86-2)

Guidance literature:

DOI:10.1016/S0008-6215(00)81066-6

Reference yield: 71.0%

phthalic anhydride (85-44-9) + 1-propenyl 2-amino-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (82185-85-1) → 1-propenyl 3,6-di-O-benzyl-2-(2-carboxybenzamido)-2-deoxy-α-D-glucopyranoside (82185-86-2)

Guidance literature:

In methanol; at 50 - 60 ℃;

DOI:10.1016/0008-6215(84)85414-2

Reference yield: 100.0%

N-{(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-hydroxy-2-[((E)-propenyl)oxy]-tetrahydro-pyran-3-yl}-phthalamic acid (82185-86-2) → 3,6-di-O-benzyl-2-(2-carboxybenzamido)-2-deoxy-D-glucose

Guidance literature:

With mercury dichloride; In water; acetone;

DOI:10.1016/S0008-6215(00)81066-6

upstream raw materials:

phthalic anhydride

(2R,3S,4R,5R,6S)-5-Amino-4-benzyloxy-2-benzyloxymethyl-6-[((E)-propenyl)oxy]-tetrahydro-pyran-3-ol

1-propenyl 2-amino-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Downstream raw materials:

1,4-di-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-α,β-D-glucopyranose

allyl 2-acetamido-4-O-(2-acetamido-4-O-acetyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-α,β-D-glucopyranose

allyl 2-acetamido-4-O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

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