methyl <2S-<2α(S^*),3β,5β,6β>>-tetrahydro-α,3,5-trimethyl-6-<<<(4-methylphenyl)sulfonyl>oxy>methyl>-2H-pyran-2-acetate

Base Information

• Chemical Name: methyl <2S-<2α(S^*),3β,5β,6β>>-tetrahydro-α,3,5-trimethyl-6-<<<(4-methylphenyl)sulfonyl>oxy>methyl>-2H-pyran-2-acetate
• CAS No.: 75830-65-8
• Molecular Formula: C₁₉H₂₈O₆S
• Molecular Weight: 384.494

Synonyms:methyl <2S-<2α(S^*),3β,5β,6β>>-tetrahydro-α,3,5-trimethyl-6-<<<(4-methylphenyl)sulfonyl>oxy>methyl>-2H-pyran-2-acetate

Chemical Property of methyl <2S-<2α(S^*),3β,5β,6β>>-tetrahydro-α,3,5-trimethyl-6-<<<(4-methylphenyl)sulfonyl>oxy>methyl>-2H-pyran-2-acetate

Chemical Property:

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Technology Process of methyl <2S-<2α(S^*),3β,5β,6β>>-tetrahydro-α,3,5-trimethyl-6-<<<(4-methylphenyl)sulfonyl>oxy>methyl>-2H-pyran-2-acetate

There total 11 articles about methyl <2S-<2α(S^*),3β,5β,6β>>-tetrahydro-α,3,5-trimethyl-6-<<<(4-methylphenyl)sulfonyl>oxy>methyl>-2H-pyran-2-acetate 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%

methyl <2S-<2α(S*),3β,5β,6β>>-tetrahydro-6-(hydroxymethyl)-α,3,5-trimethyl-2H-pyran-2-acetate (75830-64-7) + p-toluenesulfonyl chloride (98-59-9) → methyl <2S-<2α(S*),3β,5β,6β>>-tetrahydro-α,3,5-trimethyl-6-<<<(4-methylphenyl)sulfonyl>oxy>methyl>-2H-pyran-2-acetate (75830-65-8)

Guidance literature:

In pyridine; at 3 ℃; for 24h;

DOI:10.1021/jo00316a001

Reference yield:

1,5-anhydro-3-deoxy-4,6-O-phenylmethylene-3-O-propanoyl-D-ribo-hex-1-enitol (72233-95-5,88243-83-8) → methyl <2S-<2α(S*),3β,5β,6β>>-tetrahydro-α,3,5-trimethyl-6-<<<(4-methylphenyl)sulfonyl>oxy>methyl>-2H-pyran-2-acetate (75830-65-8)

Guidance literature:

Multi-step reaction with 10 steps

1: lithium diisopropylamide

3: 100 percent / 0.01 N sulfuric acid / tetrahydrofuran / 3 h / 60 °C

4: 96.5 percent / pyridine / 0 °C

5: 100 percent / pyridinium dichromate / CH₂Cl₂ / Ambient temperature

6: 100 percent / diethyl ether / 0 °C

7: 78 percent / tetrahydrofuran / 1.) -78 deg C 5 min 2.) room temp. 2 h

8: 89 percent / hydrogen / platinum oxide / pentane / 8 h / Ambient temperature

9: 97 percent / tetrabutyl ammonium fluoride / tetrahydrofuran / 2.5 h / Ambient temperature

10: 100 percent / pyridine / 24 h / 3 °C

With dipyridinium dichromate; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; pentane;

DOI:10.1021/jo00316a001

Reference yield:

1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enopyranose (63598-38-9,167074-37-5) → methyl <2S-<2α(S*),3β,5β,6β>>-tetrahydro-α,3,5-trimethyl-6-<<<(4-methylphenyl)sulfonyl>oxy>methyl>-2H-pyran-2-acetate (75830-65-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 93 percent / pyridine / DMAP / CH₂Cl₂

2: lithium diisopropylamide

4: 100 percent / 0.01 N sulfuric acid / tetrahydrofuran / 3 h / 60 °C

5: 96.5 percent / pyridine / 0 °C

6: 100 percent / pyridinium dichromate / CH₂Cl₂ / Ambient temperature

7: 100 percent / diethyl ether / 0 °C

8: 78 percent / tetrahydrofuran / 1.) -78 deg C 5 min 2.) room temp. 2 h

9: 89 percent / hydrogen / platinum oxide / pentane / 8 h / Ambient temperature

10: 97 percent / tetrabutyl ammonium fluoride / tetrahydrofuran / 2.5 h / Ambient temperature

11: 100 percent / pyridine / 24 h / 3 °C

With pyridine; dipyridinium dichromate; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen; lithium diisopropyl amide; dmap; platinum(IV) oxide; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; pentane;

DOI:10.1021/jo00316a001

upstream raw materials:

methyl <2S-<2α(S^*),3β,5β,6β>>-tetrahydro-6-(hydroxymethyl)-α,3,5-trimethyl-2H-pyran-2-acetate

p-toluenesulfonyl chloride

1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enopyranose

1,5-anhydro-3-deoxy-4,6-O-phenylmethylene-3-O-propanoyl-D-ribo-hex-1-enitol

Downstream raw materials:

(+)-Prelog-Djerassi lactonic acid

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