Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 87735-48-6
• Molecular Formula: C₃₄H₄₄O₁₁
• Molecular Weight: 628.717

Synonyms:

Chemical Property of Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester

There total 6 articles about Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-2-methyl-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:

2-O-benzyl-3,4-di-O-(p-nitrobenzoyl)-α-L-fucopyranosyl bromide (37813-15-3) → Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester (87735-48-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) mercuric cyanide, 2.) NaOMe / 1.) nitromethane-benzene, 30 h, room temp., 2.) chloroform-methanol

2: 1) NaH, 2) pyridine / 1.) DMF, 1 h, room temp.

With pyridine; sodium methylate; mercury(II) cyanide; sodium hydride;

DOI:10.1016/0008-6215(83)84046-4

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester (87735-48-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) mercuric cyanide, 2.) NaOMe / 1.) nitromethane-benzene, 30 h, room temp., 2.) chloroform-methanol

2: 1) NaH, 2) pyridine / 1.) DMF, 1 h, room temp.

With pyridine; sodium methylate; mercury(II) cyanide; sodium hydride;

DOI:10.1016/0008-6215(83)84046-4

Reference yield:

benzyl bromide (100-39-0) → Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester (87735-48-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 58.5 percent / dibutyltin oxide, tetrabutylammonium iodide / benzene / Heating

2: pyridine

With pyridine; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; In benzene;

DOI:10.1016/0008-6215(83)84046-4

upstream raw materials:

acetic anhydride

benzyl bromide

3-O-(2-O-benzyl-α-L-fucopyranosyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

3-O-(2,3-di-O-benzyl-α-L-fucopyranosyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

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