1,4-di-O-benzyl-c-3-<3-(tert-butyldiphenylsilyloxy)2-O-(p-toluolsulfonyl)prop-1-ynyl>cyclohexane-r-1,t-2,c-4-triol

Base Information

• Chemical Name: 1,4-di-O-benzyl-c-3-<3-(tert-butyldiphenylsilyloxy)2-O-(p-toluolsulfonyl)prop-1-ynyl>cyclohexane-r-1,t-2,c-4-triol
• CAS No.: 142532-51-2
• Molecular Formula: C₄₆H₅₀O₆SSi
• Molecular Weight: 759.051

Synonyms:1,4-di-O-benzyl-c-3-<3-(tert-butyldiphenylsilyloxy)2-O-(p-toluolsulfonyl)prop-1-ynyl>cyclohexane-r-1,t-2,c-4-triol

Chemical Property of 1,4-di-O-benzyl-c-3-<3-(tert-butyldiphenylsilyloxy)2-O-(p-toluolsulfonyl)prop-1-ynyl>cyclohexane-r-1,t-2,c-4-triol

Chemical Property:

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Technology Process of 1,4-di-O-benzyl-c-3-<3-(tert-butyldiphenylsilyloxy)2-O-(p-toluolsulfonyl)prop-1-ynyl>cyclohexane-r-1,t-2,c-4-triol

There total 7 articles about 1,4-di-O-benzyl-c-3-<3-(tert-butyldiphenylsilyloxy)2-O-(p-toluolsulfonyl)prop-1-ynyl>cyclohexane-r-1,t-2,c-4-triol 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: 96.0%

p-toluenesulfonylanhydride (4124-41-8) + 1,4-di-O-benzyl-c-3-<3-(tert-butyldiphenylsilyloxy)prop-1-ynyl>cyclohexane-r-1,t-2,c-4-triol (142532-47-6) → 1,4-di-O-benzyl-c-3-<3-(tert-butyldiphenylsilyloxy)2-O-(p-toluolsulfonyl)prop-1-ynyl>cyclohexane-r-1,t-2,c-4-triol (142532-51-2)

Guidance literature:

With pyridine; at 0 ℃; for 2h;

DOI:10.1039/P19920001229

Reference yield:

cyclohexa-1,3-diene (1165952-91-9) → 1,4-di-O-benzyl-c-3-<3-(tert-butyldiphenylsilyloxy)2-O-(p-toluolsulfonyl)prop-1-ynyl>cyclohexane-r-1,t-2,c-4-triol (142532-51-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) O₂, 2) thiourea / 1) 5,10,15,20-tetraphenyl-21H,23H-porphine / 1) CH₂Cl₂, -10 deg C, 5.5 h, 2) MeOH, room temperature, overnight

2: 1) sodium hydride / 1) DMF, 0 deg C, 1 h, 2) 3 h

3: 75 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 96 h / Ambient temperature

5: 96 percent / pyridine / 2 h / 0 °C

With pyridine; oxygen; sodium hydride; thiourea; 3-chloro-benzenecarboperoxoic acid; 5,15,10,20-tetraphenylporphyrin; In dichloromethane;

DOI:10.1039/P19920001229

Reference yield:

(1S,4R)-Cyclohex-2-ene-1,4-diol (53762-85-9) → 1,4-di-O-benzyl-c-3-<3-(tert-butyldiphenylsilyloxy)2-O-(p-toluolsulfonyl)prop-1-ynyl>cyclohexane-r-1,t-2,c-4-triol (142532-51-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) sodium hydride / 1) DMF, 0 deg C, 1 h, 2) 3 h

2: 75 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 96 h / Ambient temperature

4: 96 percent / pyridine / 2 h / 0 °C

With pyridine; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1039/P19920001229

upstream raw materials:

p-toluenesulfonylanhydride

1,4-di-O-benzyl-c-3-<3-(tert-butyldiphenylsilyloxy)prop-1-ynyl>cyclohexane-r-1,t-2,c-4-triol

(1S,4R)-Cyclohex-2-ene-1,4-diol

tert-butyl(diphenyl)(2-propynyloxy)silane

Downstream raw materials:

c-3-(3-iodoprop-1-ynyl)-2-O-(p-tolyl)-cyclohexane-r-1,t-2,c-4-triol

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