2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-5-((2S,3R,4S,5R,6R)-4-benzyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Base Information

• Chemical Name: 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-5-((2S,3R,4S,5R,6R)-4-benzyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione
• CAS No.: 322479-14-1
• Molecular Formula: C₄₃H₄₇NO₁₁S
• Molecular Weight: 785.912

Synonyms:

Chemical Property of 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-5-((2S,3R,4S,5R,6R)-4-benzyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Chemical Property:

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Safty Information:

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Useful:

Technology Process of 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-5-((2S,3R,4S,5R,6R)-4-benzyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

There total 3 articles about 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-5-((2S,3R,4S,5R,6R)-4-benzyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione 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:

ethyl (2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (322479-13-0) → 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-5-((2S,3R,4S,5R,6R)-4-benzyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (322479-14-1)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1002/1099-0690(200012)2000:23<3931::AID-EJOC3931>3.0.CO;2-W

Reference yield:

2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranosyl bromide (34339-69-0) → 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-5-((2S,3R,4S,5R,6R)-4-benzyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (322479-14-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / 4A MS; silver triflate / CH₂Cl₂; toluene / 1 h / -40 °C

2: sodium methoxide / methanol

With sodium methylate; silver trifluoromethanesulfonate; In methanol; dichloromethane; toluene; 2: Zemplen deacetylation;

DOI:10.1002/1099-0690(200012)2000:23<3931::AID-EJOC3931>3.0.CO;2-W

Reference yield:

ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (115533-35-2) → 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-5-((2S,3R,4S,5R,6R)-4-benzyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (322479-14-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / 4A MS; silver triflate / CH₂Cl₂; toluene / 1 h / -40 °C

2: sodium methoxide / methanol

With sodium methylate; silver trifluoromethanesulfonate; In methanol; dichloromethane; toluene; 2: Zemplen deacetylation;

DOI:10.1002/1099-0690(200012)2000:23<3931::AID-EJOC3931>3.0.CO;2-W

upstream raw materials:

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

2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranosyl bromide

ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Downstream raw materials:

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

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