Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-3,5-dihydroxy-4-(4-methoxy-benzyloxy)-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-3,5-dihydroxy-4-(4-methoxy-benzyloxy)-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 335275-37-1
• Molecular Formula: C₅₄H₆₄O₁₄S
• Molecular Weight: 969.16

Synonyms:Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-3,5-dihydroxy-4-(4-methoxy-benzyloxy)-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-3,5-dihydroxy-4-(4-methoxy-benzyloxy)-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-2-ylmethyl ester

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Technology Process of Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-3,5-dihydroxy-4-(4-methoxy-benzyloxy)-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-2-ylmethyl ester

There total 3 articles about Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-3,5-dihydroxy-4-(4-methoxy-benzyloxy)-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-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: 75.0%

p-toluenesulfonyl chloride (98-59-9) + (2R,3S,4S,5R,6R)-2-Hydroxymethyl-4-(4-methoxy-benzyloxy)-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,5-diol (335275-36-0) → Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-3,5-dihydroxy-4-(4-methoxy-benzyloxy)-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-2-ylmethyl ester (335275-37-1)

Guidance literature:

With pyridine; In dichloromethane; for 17h; Heating;

DOI:10.1016/S0960-894X(00)00692-2

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-3,5-dihydroxy-4-(4-methoxy-benzyloxy)-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-2-ylmethyl ester (335275-37-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Bu₂SnO / benzene / 5 h / Heating

1.2: 81 percent / Bu₄NBr / benzene / 6 h / 60 °C

2.1: 75 percent / pyridine / CH₂Cl₂ / 17 h / Heating

With pyridine; di(n-butyl)tin oxide; In dichloromethane; benzene;

DOI:10.1016/S0960-894X(00)00692-2

Reference yield:

(2R,3R,4S,5R,6R)-2-Hydroxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4,5-triol (172147-75-0) → Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-3,5-dihydroxy-4-(4-methoxy-benzyloxy)-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-2-ylmethyl ester (335275-37-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Bu₂SnO / benzene / 5 h / Heating

1.2: 81 percent / Bu₄NBr / benzene / 6 h / 60 °C

2.1: 75 percent / pyridine / CH₂Cl₂ / 17 h / Heating

With pyridine; di(n-butyl)tin oxide; In dichloromethane; benzene;

DOI:10.1016/S0960-894X(00)00692-2

upstream raw materials:

p-toluenesulfonyl chloride

(2R,3S,4S,5R,6R)-2-Hydroxymethyl-4-(4-methoxy-benzyloxy)-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,5-diol

p-Methoxybenzyl bromide

(2R,3R,4S,5R,6R)-2-Hydroxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4,5-triol

Downstream raw materials:

(S)-2-{(2R,3S,4S,5R,6R)-2-Azidomethyl-3,5-dihydroxy-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yloxy}-3-phenyl-propionic acid benzyl ester

(2R,3R,4S,5R,6R)-2-Azidomethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4,5-triol

(S)-2-{(2R,3S,4S,5R,6R)-2-Aminomethyl-3,5-dihydroxy-6-[(1R,2R)-2-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yloxy}-3-phenyl-propionic acid

(2R,3S,4S,5R,6R)-2-Azidomethyl-4-(4-methoxy-benzyloxy)-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,5-diol

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