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

Base Information

• Chemical Name: Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-2-((2R,3R,4R,5S,6S)-2,3-bis-allyloxy-5-benzyloxy-6-methyl-tetrahydro-pyran-4-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 144174-55-0
• Molecular Formula: C₃₁H₄₂O₁₂
• Molecular Weight: 606.667

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

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

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

There total 4 articles about Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-2-((2R,3R,4R,5S,6S)-2,3-bis-allyloxy-5-benzyloxy-6-methyl-tetrahydro-pyran-4-yloxy)-6-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: 66.0%

(2R,3R,4R,5R,6S)-2,3-Bis-allyloxy-5-benzyloxy-6-methyl-tetrahydro-pyran-4-ol (144174-54-9) + 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide (5158-64-5) → Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-2-((2R,3R,4R,5S,6S)-2,3-bis-allyloxy-5-benzyloxy-6-methyl-tetrahydro-pyran-4-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester (144174-55-0)

Guidance literature:

With 4 A molecular sieve; mercury(II) cyanide; mercury dibromide; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4020(01)80018-1

Reference yield:

allyl 4-O-benzyl-α-L-rhamnopyranoside (89821-78-3) → Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-2-((2R,3R,4R,5S,6S)-2,3-bis-allyloxy-5-benzyloxy-6-methyl-tetrahydro-pyran-4-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester (144174-55-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) toluene, reflux, 3 h, 2) DMF, 90 deg C, 3 h

2: 1) sodium hydride / 1) THF, oil, 2 h, 2) 18 h

3: 83 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂ / 0.5 h / Ambient temperature

4: 66 percent / mercuric cyanide, mercuric bromide, molecular sieves (4 Angstroem) / CH₂Cl₂ / Ambient temperature

With 4 A molecular sieve; mercury(II) cyanide; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; mercury dibromide; In dichloromethane;

DOI:10.1016/S0040-4020(01)80018-1

Reference yield:

allyl 2-O-allyl-4-O-benzyl-3-O-p-methoxybenzyl-α-L-rhamnopyranoside (144174-53-8) → Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-2-((2R,3R,4R,5S,6S)-2,3-bis-allyloxy-5-benzyloxy-6-methyl-tetrahydro-pyran-4-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester (144174-55-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 66 percent / mercuric cyanide, mercuric bromide, molecular sieves (4 Angstroem) / CH₂Cl₂ / Ambient temperature

With 4 A molecular sieve; mercury(II) cyanide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; mercury dibromide; In dichloromethane;

DOI:10.1016/S0040-4020(01)80018-1

upstream raw materials:

(2R,3R,4R,5R,6S)-2,3-Bis-allyloxy-5-benzyloxy-6-methyl-tetrahydro-pyran-4-ol

2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide

allyl 4-O-benzyl-α-L-rhamnopyranoside

allyl 4-O-benzyl-3-O-para-methoxybenzyl-α-L-rhamnopyranoside

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