Acetic acid (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-{(3aR,4S,6S,7S,7aR)-2,2,6-trimethyl-4-[4-(2,2,2-trifluoro-acetylamino)-phenoxy]-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy}-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-{(3aR,4S,6S,7S,7aR)-2,2,6-trimethyl-4-[4-(2,2,2-trifluoro-acetylamino)-phenoxy]-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy}-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 87424-11-1
• Molecular Formula: C₄₆H₅₀F₃NO₁₂
• Molecular Weight: 865.898
• Mol file: 87424-11-1.mol

Synonyms:

Chemical Property of Acetic acid (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-{(3aR,4S,6S,7S,7aR)-2,2,6-trimethyl-4-[4-(2,2,2-trifluoro-acetylamino)-phenoxy]-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy}-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-{(3aR,4S,6S,7S,7aR)-2,2,6-trimethyl-4-[4-(2,2,2-trifluoro-acetylamino)-phenoxy]-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy}-tetrahydro-pyran-2-ylmethyl ester

There total 4 articles about Acetic acid (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-{(3aR,4S,6S,7S,7aR)-2,2,6-trimethyl-4-[4-(2,2,2-trifluoro-acetylamino)-phenoxy]-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy}-tetrahydro-pyran-2-ylmethyl 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%

6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl bromide (70056-63-2) + p-trifluoroacetamidophenyl 2,3-O-isopropylidene-α-L-rhamnopyranoside (87424-09-7) → p-trifluoroacetamidophenyl 4-O-(6-O-acetyl-2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranoside (87424-10-0) + Acetic acid (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-{(3aR,4S,6S,7S,7aR)-2,2,6-trimethyl-4-[4-(2,2,2-trifluoro-acetylamino)-phenoxy]-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy}-tetrahydro-pyran-2-ylmethyl ester (87424-11-1)

Guidance literature:

silver zeolite; In dichloromethane; for 20h;

DOI:10.1016/0008-6215(83)84048-8

Reference yield:

p-trifluoroacetamidophenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranoside (87735-63-5) → Acetic acid (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-{(3aR,4S,6S,7S,7aR)-2,2,6-trimethyl-4-[4-(2,2,2-trifluoro-acetylamino)-phenoxy]-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy}-tetrahydro-pyran-2-ylmethyl ester (87424-11-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaOMe, 2.) p-TsOH / 1.) MeOH, room temp., 3h, 2.) acetone, room temp., 6h

2: 9 percent / silver zeolite / CH₂Cl₂ / 20 h

With sodium methylate; toluene-4-sulfonic acid; silver zeolite; In dichloromethane;

DOI:10.1016/0008-6215(83)84048-8

Reference yield:

2,2-dimethoxy-propane (77-76-9) → Acetic acid (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-{(3aR,4S,6S,7S,7aR)-2,2,6-trimethyl-4-[4-(2,2,2-trifluoro-acetylamino)-phenoxy]-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy}-tetrahydro-pyran-2-ylmethyl ester (87424-11-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaOMe, 2.) p-TsOH / 1.) MeOH, room temp., 3h, 2.) acetone, room temp., 6h

2: 9 percent / silver zeolite / CH₂Cl₂ / 20 h

With sodium methylate; toluene-4-sulfonic acid; silver zeolite; In dichloromethane;

DOI:10.1016/0008-6215(83)84048-8

upstream raw materials:

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

p-trifluoroacetamidophenyl 2,3-O-isopropylidene-α-L-rhamnopyranoside

p-trifluoroacetamidophenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranoside

2,2-dimethoxy-propane