Acetic acid (2S,3S,4R,5R,6S)-6-[(2S,3S,4R,5R,6S)-6-((2S,3S,4R,5R,6R)-6-allyloxy-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3S,4R,5R,6S)-6-[(2S,3S,4R,5R,6S)-6-((2S,3S,4R,5R,6R)-6-allyloxy-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 138824-96-1
• Molecular Formula: C₆₅H₇₄O₁₄
• Molecular Weight: 1079.29

Synonyms:Acetic acid (2S,3S,4R,5R,6S)-6-[(2S,3S,4R,5R,6S)-6-((2S,3S,4R,5R,6R)-6-allyloxy-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3S,4R,5R,6S)-6-[(2S,3S,4R,5R,6S)-6-((2S,3S,4R,5R,6R)-6-allyloxy-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2S,3S,4R,5R,6S)-6-[(2S,3S,4R,5R,6S)-6-((2S,3S,4R,5R,6R)-6-allyloxy-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yl ester

There total 12 articles about Acetic acid (2S,3S,4R,5R,6S)-6-[(2S,3S,4R,5R,6S)-6-((2S,3S,4R,5R,6R)-6-allyloxy-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-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: 52.0%

Acetic acid (2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-6-chloro-2-methyl-tetrahydro-pyran-3-yl ester (138824-94-9) + (2S,3S,4R,5R,6S)-6-((2S,3S,4R,5R,6R)-6-Allyloxy-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-ol (127085-19-2) → Acetic acid (2S,3S,4R,5R,6S)-6-[(2S,3S,4R,5R,6S)-6-((2S,3S,4R,5R,6R)-6-allyloxy-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yl ester (138824-96-1)

Guidance literature:

With isopropenylbenzene; at 70 ℃; for 40h;

DOI:10.1016/0040-4039(91)80081-G

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → Acetic acid (2S,3S,4R,5R,6S)-6-[(2S,3S,4R,5R,6S)-6-((2S,3S,4R,5R,6R)-6-allyloxy-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yl ester (138824-96-1)

Guidance literature:

Multi-step reaction with 7 steps

3: 1.) diisobutylaluminium hydride, 2.) NaH / 1.) CH₂Cl₂, 2.) DMF, THF

4: 92 percent / aq. HF / acetonitrile

5: 60 percent / α-methylstyrene / 15 h / 70 °C

6: CH₃ONa / methanol

7: 52 percent / α-methylstyrene / 40 h / 70 °C

With hydrogen fluoride; sodium methylate; sodium hydride; diisobutylaluminium hydride; isopropenylbenzene; In methanol; acetonitrile;

DOI:10.1016/0040-4039(91)80081-G

Reference yield:

allyl α-L-rhamnopyranoside (64650-81-3) → Acetic acid (2S,3S,4R,5R,6S)-6-[(2S,3S,4R,5R,6S)-6-((2S,3S,4R,5R,6R)-6-allyloxy-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yl ester (138824-96-1)

Guidance literature:

Multi-step reaction with 7 steps

3: 1.) diisobutylaluminium hydride, 2.) NaH / 1.) CH₂Cl₂, 2.) DMF, THF

4: 92 percent / aq. HF / acetonitrile

5: 60 percent / α-methylstyrene / 15 h / 70 °C

6: CH₃ONa / methanol

7: 52 percent / α-methylstyrene / 40 h / 70 °C

With hydrogen fluoride; sodium methylate; sodium hydride; diisobutylaluminium hydride; isopropenylbenzene; In methanol; acetonitrile;

DOI:10.1016/0040-4039(91)80081-G

upstream raw materials:

Acetic acid (2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-6-chloro-2-methyl-tetrahydro-pyran-3-yl ester

(2S,3S,4R,5R,6S)-6-((2S,3S,4R,5R,6R)-6-Allyloxy-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-ol

allyl α-L-rhamnopyranoside

benzaldehyde dimethyl acetal

Downstream raw materials:

(2S,3S,4R,5R,6S)-6-[(2S,3S,4R,5R,6S)-6-((2S,3S,4R,5R,6R)-6-Allyloxy-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-ol

Acetic acid (2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-6-[(2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-6-((2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-6-chloro-2-methyl-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester

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