Acetic acid (2R,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-5-((2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-5-((2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester
• CAS No.: 205987-10-6
• Molecular Formula: C₅₃H₅₅NO₁₃
• Molecular Weight: 914.019

Synonyms:Acetic acid (2R,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-5-((2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-5-((2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

Chemical Property:

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Technology Process of Acetic acid (2R,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-5-((2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

There total 3 articles about Acetic acid (2R,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-5-((2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-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: 9.0%

1,2-anhydro-3,4,6-tri-O-benzyl-D-galactopyranose (112289-38-0) + allyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (157567-42-5) → Acetic acid (2R,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-5-((2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester (205987-10-6)

Guidance literature:

With 4 A molecular sieve; lithium perchlorate; In dichloromethane; for 72h; Ambient temperature;

DOI:10.1002/(SICI)1521-3765(19980310)4:3<494::AID-CHEM494>3.0.CO;2-8

Reference yield:

allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (120142-50-9) → Acetic acid (2R,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-5-((2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester (205987-10-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / pyridine / 18 h / Ambient temperature

2: 72 percent / BH₃*NMe₃, AlCl₃, 4 Angstroem molecular sieves / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) r.t., 2 h

3: 9 percent / LiClO₄, 4 Agstroem molecular sieves / CH₂Cl₂ / 72 h / Ambient temperature

With pyridine; aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; lithium perchlorate; In tetrahydrofuran; dichloromethane;

DOI:10.1002/(SICI)1521-3765(19980310)4:3<494::AID-CHEM494>3.0.CO;2-8

Reference yield:

allyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (202600-40-6) → Acetic acid (2R,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-5-((2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester (205987-10-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / BH₃*NMe₃, AlCl₃, 4 Angstroem molecular sieves / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) r.t., 2 h

2: 9 percent / LiClO₄, 4 Agstroem molecular sieves / CH₂Cl₂ / 72 h / Ambient temperature

With aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; lithium perchlorate; In tetrahydrofuran; dichloromethane;

DOI:10.1002/(SICI)1521-3765(19980310)4:3<494::AID-CHEM494>3.0.CO;2-8

upstream raw materials:

1,2-anhydro-3,4,6-tri-O-benzyl-D-galactopyranose

allyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

allyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

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