Toluene-4-sulfonic acid (2S,5R,6S)-5-methoxy-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2S,5R,6S)-5-methoxy-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester
• CAS No.: 182622-54-4
• Molecular Formula: C₁₈H₂₆O₆S
• Molecular Weight: 370.467

Synonyms:Toluene-4-sulfonic acid (2S,5R,6S)-5-methoxy-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester

Chemical Property of Toluene-4-sulfonic acid (2S,5R,6S)-5-methoxy-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of Toluene-4-sulfonic acid (2S,5R,6S)-5-methoxy-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester

There total 22 articles about Toluene-4-sulfonic acid (2S,5R,6S)-5-methoxy-1,7-dioxa-spiro[5.5]undec-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: 100.0%

p-toluenesulfonyl chloride (98-59-9) + ((2S,5R,6S)-5-Methoxy-1,7-dioxa-spiro[5.5]undec-2-yl)-methanol (182622-52-2) → Toluene-4-sulfonic acid (2S,5R,6S)-5-methoxy-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester (182622-54-4)

Guidance literature:

With pyridine;

DOI:10.1016/0040-4039(96)01265-8

Reference yield:

benzyl α-D-galactopyranoside (86196-36-3) → Toluene-4-sulfonic acid (2S,5R,6S)-5-methoxy-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester (182622-54-4)

Guidance literature:

Multi-step reaction with 16 steps

1: TsOH / acetone / 7 h / 0 °C

2: pyridine / 20 h / Ambient temperature

3: 80 percent / aq. AcOH / 4 h / 50 °C

4: 90 percent / acetonitrile / 5 h / Ambient temperature

5: 80 percent / trimethyl phosphite / 4.5 h / Heating

6: 85 percent / H₂ / Pd(OH)2/C / ethanol / 5 h / Ambient temperature

7: 100 percent / K₂CO₃ / methanol / 3 h / Ambient temperature

8: 79 percent / imidazole / dimethylformamide / 0.08 h / Ambient temperature

9: 87 percent / NaOH / acetone / 2 h / Heating

10: 74 percent / BCl₃*SMe₂ / CH₂Cl₂ / 14 h / Ambient temperature

11: 105 mg / CCl₄, Ph₃P / tetrahydrofuran / 3 h / Heating

12: 16 percent / diethyl ether / 1 h / 0 °C

13: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) CH₂Cl₂, MeOH, room temp., 12 h

14: 48 percent / (diacetoxyiodo)benzene, I₂ / cyclohexane / 1.17 h / 40 °C / Irradiation

15: 88 percent / Bu₄NF / tetrahydrofuran / 2.5 h / Ambient temperature

16: 100 percent / pyridine / 15 h / Ambient temperature

With 1H-imidazole; tetrachloromethane; sodium hydroxide; sodium tetrahydroborate; [bis(acetoxy)iodo]benzene; boron trichloride - methyl sulfide complex; tetrabutyl ammonium fluoride; hydrogen; iodine; potassium carbonate; toluene-4-sulfonic acid; ozone; acetic acid; triphenylphosphine; phosphorous acid trimethyl ester; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; cyclohexane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/jo972023a

Reference yield:

Acetic acid (2S,3R,6S)-6-acetoxymethyl-2-benzyloxy-3,6-dihydro-2H-pyran-3-yl ester (182622-31-7) → Toluene-4-sulfonic acid (2S,5R,6S)-5-methoxy-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester (182622-54-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 85 percent / H₂ / Pd(OH)2/C / ethanol / 5 h / Ambient temperature

2: 100 percent / K₂CO₃ / methanol / 3 h / Ambient temperature

3: 79 percent / imidazole / dimethylformamide / 0.08 h / Ambient temperature

4: 87 percent / NaOH / acetone / 2 h / Heating

5: 74 percent / BCl₃*SMe₂ / CH₂Cl₂ / 14 h / Ambient temperature

6: 105 mg / CCl₄, Ph₃P / tetrahydrofuran / 3 h / Heating

7: 16 percent / diethyl ether / 1 h / 0 °C

8: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) CH₂Cl₂, MeOH, room temp., 12 h

9: 48 percent / (diacetoxyiodo)benzene, I₂ / cyclohexane / 1.17 h / 40 °C / Irradiation

10: 88 percent / Bu₄NF / tetrahydrofuran / 2.5 h / Ambient temperature

11: 100 percent / pyridine / 15 h / Ambient temperature

With 1H-imidazole; tetrachloromethane; sodium hydroxide; sodium tetrahydroborate; [bis(acetoxy)iodo]benzene; boron trichloride - methyl sulfide complex; tetrabutyl ammonium fluoride; hydrogen; iodine; potassium carbonate; ozone; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; cyclohexane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo972023a

upstream raw materials:

p-toluenesulfonyl chloride

((2S,5R,6S)-5-Methoxy-1,7-dioxa-spiro[5.5]undec-2-yl)-methanol

benzyl α-D-galactopyranoside

(2S,3R,6S)-2-Benzyloxy-6-hydroxymethyl-tetrahydro-pyran-3-ol

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