Acetic acid (2R,3S,4R,5R,6R)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4R,5R,6R)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yl ester
• CAS No.: 493027-46-6
• Molecular Formula: C₂₈H₃₅NO₈Si
• Molecular Weight: 541.673

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

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

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

There total 1 articles about Acetic acid (2R,3S,4R,5R,6R)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-6-(2-trimethylsilanyl-ethoxy)-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: 66.0%

2-(trimethylsilyl)ethyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside → Acetic acid (2R,3S,4R,5R,6R)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yl ester (493027-46-6)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1016/S0040-4039(02)01795-1

Reference yield: 85.0%

2,3,4,6-tetra-O-benzoyl-α,b-D-galactopyranosyl trichloroacetimidate (203435-09-0) + Acetic acid (2R,3S,4R,5R,6R)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yl ester (493027-46-6) → C62H61NO17Si (493027-47-7)

Guidance literature:

With trifluorormethanesulfonic acid; 4 A molecular sieve; In 1,2-dichloro-ethane; at 55 ℃; for 1.5h;

DOI:10.1016/S0040-4039(02)01795-1

Reference yield:

Acetic acid (2R,3S,4R,5R,6R)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yl ester (493027-46-6) → C57H49NO17

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / TfOH; molecular sieves 4 Angstroem / 1,2-dichloro-ethane / 1.5 h / 55 °C

2: TFA / CH₂Cl₂

With trifluorormethanesulfonic acid; 4 A molecular sieve; trifluoroacetic acid; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1016/S0040-4039(02)01795-1

Downstream raw materials:

C₆₂H₆₁NO₁₇Si

C₅₉H₄₉Cl₃N₂O₁₇

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