Trifluoro-methanesulfonic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Trifluoro-methanesulfonic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 213028-99-0
• Molecular Formula: C₅₆H₅₉F₃O₁₃S
• Molecular Weight: 1029.14

Synonyms:

Chemical Property of Trifluoro-methanesulfonic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester

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Technology Process of Trifluoro-methanesulfonic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester

There total 14 articles about Trifluoro-methanesulfonic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-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:

trifluoromethylsulfonic anhydride (358-23-6) + methyl 3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside (98906-49-1) → Trifluoro-methanesulfonic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester (213028-99-0)

Guidance literature:

With pyridine; In dichloromethane; Yield given; Ambient temperature;

DOI:10.1016/S0040-4039(98)01163-0

Reference yield:

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) → Trifluoro-methanesulfonic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester (213028-99-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 38.5 percent / tetraethylammonium perchlorate; (1S)-(+)-10 camphorsulfonic acid / 1,2-dichloro-ethane / 2 h / Heating

2: 98 percent / NaOMe / methanol

3: pyridine / CH₂Cl₂ / 3 h / 20 °C

With pyridine; sodium methylate; tetraethylammonium perchlorate; (+)-10-camphorsulfonic acid; In methanol; dichloromethane; 1,2-dichloro-ethane; 2: Zemplen reaction;

DOI:10.3987/COM-03-S60

Reference yield:

methyl 2-O-acetyl-3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-1→4-(2,3,6-tri-O-benzyl)-β-D-glucopyranoside (98906-48-0) → Trifluoro-methanesulfonic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester (213028-99-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / NaOMe / methanol

2: pyridine / CH₂Cl₂ / 3 h / 20 °C

With pyridine; sodium methylate; In methanol; dichloromethane; 1: Zemplen reaction;

DOI:10.3987/COM-03-S60

upstream raw materials:

trifluoromethylsulfonic anhydride

methyl 3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

benzyl bromide

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