Acetic acid (2S,4S,5R,6S)-4,5-bis-benzyloxy-6-((2S,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Acetic acid (2S,4S,5R,6S)-4,5-bis-benzyloxy-6-((2S,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 174193-75-0
• Molecular Formula: C₄₃H₅₀O₁₀
• Molecular Weight: 726.864

Synonyms:Acetic acid (2S,4S,5R,6S)-4,5-bis-benzyloxy-6-((2S,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Acetic acid (2S,4S,5R,6S)-4,5-bis-benzyloxy-6-((2S,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl ester

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Technology Process of Acetic acid (2S,4S,5R,6S)-4,5-bis-benzyloxy-6-((2S,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl ester

There total 6 articles about Acetic acid (2S,4S,5R,6S)-4,5-bis-benzyloxy-6-((2S,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-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: 92.0%

methyl 2,3-di-O-benzyl-4-deoxy-6-O-trimethylsilyl-α-D-xylo-hexopyranoside (174193-62-5) + Acetic acid (3R,4S,6S)-6-acetoxymethyl-3,4-bis-benzyloxy-tetrahydro-pyran-2-yl ester → Acetic acid (2S,4S,5R,6S)-4,5-bis-benzyloxy-6-((2S,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl ester (174193-75-0)

Guidance literature:

With silver perchlorate; tin(IV) chloride; In diethyl ether; n-heptane; at 0 ℃; for 24h;

DOI:10.1016/0008-6215(95)00280-4

Reference yield:

methyl 2,3-di-O-benzyl-6-O-acetyl-α-D-glucopyranoside (20771-21-5,51842-23-0,51842-24-1,117561-20-3,125884-32-4,51842-22-9) → Acetic acid (2S,4S,5R,6S)-4,5-bis-benzyloxy-6-((2S,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl ester (174193-75-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / N-hydroxysuccinimide, pyridine / toluene / 6 h / 80 °C

2: 95 percent / tributyltin hydride, AIBN / toluene / 2 h / 90 °C

3: 91 percent / NaOMe, MeOH / toluene / 20 h / Ambient temperature

4: 91 percent / imidazole / CH₂Cl₂ / 1.5 h / 0 - 5 °C

5: 92 percent / SnCl₄, AgClO₄ / heptane; diethyl ether / 24 h / 0 °C

With pyridine; 1H-imidazole; methanol; 1-hydroxy-pyrrolidine-2,5-dione; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium methylate; silver perchlorate; tin(IV) chloride; In diethyl ether; n-heptane; dichloromethane; toluene;

DOI:10.1016/0008-6215(95)00280-4

Reference yield:

Methyl 2,3-di-O-benzyl-4-deoxy-α-D-xylo-hexopyranoside (108164-50-7) → Acetic acid (2S,4S,5R,6S)-4,5-bis-benzyloxy-6-((2S,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl ester (174193-75-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / imidazole / CH₂Cl₂ / 1.5 h / 0 - 5 °C

2: 92 percent / SnCl₄, AgClO₄ / heptane; diethyl ether / 24 h / 0 °C

With 1H-imidazole; silver perchlorate; tin(IV) chloride; In diethyl ether; n-heptane; dichloromethane;

DOI:10.1016/0008-6215(95)00280-4

upstream raw materials:

methyl 2,3-di-O-benzyl-4-deoxy-6-O-trimethylsilyl-α-D-xylo-hexopyranoside

methyl 2,3-di-O-benzyl-6-O-acetyl-α-D-glucopyranoside

Methyl 2,3-di-O-benzyl-4-deoxy-α-D-xylo-hexopyranoside

methyl 6-O-acetyl-2,3-di-O-benzyl-4-deoxy-α-D-xylo-hexopyranoside

Downstream raw materials:

[(2S,4S,5R,6S)-4,5-Bis-benzyloxy-6-((2S,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-yl]-methanol

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