Acetic acid (1R,2R,3R,4R,6S)-6-acetoxymethyl-2,3,4-tris-benzyloxy-cyclohexyl ester

Base Information

• Chemical Name: Acetic acid (1R,2R,3R,4R,6S)-6-acetoxymethyl-2,3,4-tris-benzyloxy-cyclohexyl ester
• CAS No.: 94898-39-2
• Molecular Formula: C₃₂H₃₆O₇
• Molecular Weight: 532.634

Synonyms:

Chemical Property of Acetic acid (1R,2R,3R,4R,6S)-6-acetoxymethyl-2,3,4-tris-benzyloxy-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of Acetic acid (1R,2R,3R,4R,6S)-6-acetoxymethyl-2,3,4-tris-benzyloxy-cyclohexyl ester

There total 88 articles about Acetic acid (1R,2R,3R,4R,6S)-6-acetoxymethyl-2,3,4-tris-benzyloxy-cyclohexyl 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:

(2R,3R,4R)-2,3,4-tris-benzyloxy-5,5-bis-ethylsulfanyl-pentan-1-ol (108713-89-9) → (1S,2S,3R,4S,5S)-2-acetoxy-1-(acetoxymethyl)-3,4,5-tris(benzyloxy)cyclohexane (94898-39-2,94943-05-2,102629-11-8,105368-82-9,108813-45-2,108813-46-3,108813-48-5,112531-57-4,115184-60-6,115184-63-9,125354-33-8)

Guidance literature:

Multi-step reaction with 9 steps

1: imidazole / dimethylformamide

2: mercury(II)chloride / acetonitrile; H₂O

3: 85 percent / acetic anhydride / pyridine / 48 h / Ambient temperature

4: H₂ / Raney nickel

5: tetrabutylammonium fluoride

6: 1.) PCC / 1.) CH₂Cl₂, 2.) pyridine

7: 70 percent / NaCl / dimethylsulfoxide; H₂O / 110 - 170 °C

8: 88 percent / LiAlH₄ / tetrahydrofuran / -15 °C

9: 1.) BH₃*THF, 2.) aq. NaOH, 35percent H₂O₂ / 1.) RT

With 1H-imidazole; sodium hydroxide; lithium aluminium tetrahydride; borane-THF; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; acetic anhydride; pyridinium chlorochromate; sodium chloride; mercury dichloride; nickel; In tetrahydrofuran; pyridine; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1246/cl.1986.1081

Reference yield:

C49H52O4S2 (105265-81-4) → (1S,2S,3R,4S,5S)-2-acetoxy-1-(acetoxymethyl)-3,4,5-tris(benzyloxy)cyclohexane (94898-39-2,94943-05-2,102629-11-8,105368-82-9,108813-45-2,108813-46-3,108813-48-5,112531-57-4,115184-60-6,115184-63-9,125354-33-8)

Guidance literature:

Multi-step reaction with 10 steps

1: TsOH / methanol; ethyl acetate

2: imidazole / dimethylformamide

3: mercury(II)chloride / acetonitrile; H₂O

4: 85 percent / acetic anhydride / pyridine / 48 h / Ambient temperature

5: H₂ / Raney nickel

6: tetrabutylammonium fluoride

7: 1.) PCC / 1.) CH₂Cl₂, 2.) pyridine

8: 70 percent / NaCl / dimethylsulfoxide; H₂O / 110 - 170 °C

9: 88 percent / LiAlH₄ / tetrahydrofuran / -15 °C

10: 1.) BH₃*THF, 2.) aq. NaOH, 35percent H₂O₂ / 1.) RT

With 1H-imidazole; sodium hydroxide; lithium aluminium tetrahydride; borane-THF; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; acetic anhydride; toluene-4-sulfonic acid; pyridinium chlorochromate; sodium chloride; mercury dichloride; nickel; In tetrahydrofuran; pyridine; methanol; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1246/cl.1986.1081

Reference yield:

benzyl bromide (100-39-0) → (1S,2S,3R,4S,5S)-2-acetoxy-1-(acetoxymethyl)-3,4,5-tris(benzyloxy)cyclohexane (94898-39-2,94943-05-2,102629-11-8,105368-82-9,108813-45-2,108813-46-3,108813-48-5,112531-57-4,115184-60-6,115184-63-9,125354-33-8)

Guidance literature:

Multi-step reaction with 11 steps

1: NaH / dimethylformamide

2: TsOH / methanol; ethyl acetate

3: imidazole / dimethylformamide

4: mercury(II)chloride / acetonitrile; H₂O

5: 85 percent / acetic anhydride / pyridine / 48 h / Ambient temperature

6: H₂ / Raney nickel

7: tetrabutylammonium fluoride

8: 1.) PCC / 1.) CH₂Cl₂, 2.) pyridine

9: 70 percent / NaCl / dimethylsulfoxide; H₂O / 110 - 170 °C

10: 88 percent / LiAlH₄ / tetrahydrofuran / -15 °C

11: 1.) BH₃*THF, 2.) aq. NaOH, 35percent H₂O₂ / 1.) RT

With 1H-imidazole; sodium hydroxide; lithium aluminium tetrahydride; borane-THF; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; acetic anhydride; sodium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; sodium chloride; mercury dichloride; nickel; In tetrahydrofuran; pyridine; methanol; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1246/cl.1986.1081

upstream raw materials:

benzyl bromide

2,3,4-tri-O-benzyl-D-xylose diethyl dithioacetal

2,3,4-tri-O-benzyl-5-O-(tert-butyldiphenylsilyl)-D-xylose diethyl dithioacetal

C₄₉H₅₂O₄S₂

Downstream raw materials:

(1R,2R,3R,4R,5S)-2,3,4,5-tetraacetoxy-1-(acetoxymethyl)cyclohexane, pseudo-α-D-altropyranose pentaacetate

(1S,2S,3R,4R,5S)-2,3,4,5-tetraacetoxy-1-(acetoxymethyl)cyclohexane, pseudo-β-L-glucopyranose pentaacetate

(1S,2S,3R,4S,5R)-2,3,4,5-tetraacetoxy-1-(acetoxymethyl)cyclohexane, pseudo-α-L-mannopyranose pentaacetate

(1S,2S,3R,4S,5S)-2,3,4,5-tetraacetoxy-1-(acetoxymethyl)cyclohexane, pseudo-β-L-mannopyranose pentaacetate

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