(3aR,6R,7S,7aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

Base Information

• Chemical Name: (3aR,6R,7S,7aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran
• CAS No.: 201142-47-4
• Molecular Formula: C₂₂H₂₆O₅S
• Molecular Weight: 402.511
• Mol file: 201142-47-4.mol

Synonyms:(3aR,6R,7S,7aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

Chemical Property of (3aR,6R,7S,7aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,6R,7S,7aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

There total 1 articles about (3aR,6R,7S,7aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran 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: 93.0%

p-methoxybenzyl chloride (824-94-2) + (3aR,6R,7S,7aS)-2,2-Dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol (193359-93-2) → (3aR,6R,7S,7aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran (201142-47-4)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; 1.) 0 deg C, 30 min, 2.) 2 h;

DOI:10.1002/anie.199725201

Reference yield: 84.0%

(3aR,6R,7S,7aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran (201142-47-4) → (3R,4R,5S,6R)-5-(4-Methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-3,4-diol (201142-49-6)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; ethylene glycol; at 25 ℃; for 6h;

DOI:10.1002/anie.199725201

Reference yield:

(3aR,6R,7S,7aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran (201142-47-4) → C57H102O9Si4

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / TsOH*H₂O, ethanediol / methanol / 6 h / 25 °C

2: 97 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

3: 80 percent / NBS, pyridine / acetone; H₂O

4: 93 percent / NaH / CH₂Cl₂ / 3.5 h / 25 °C

5: TMSOTf / hexane / -78 °C

6: LiHMDS / tetrahydrofuran / 0.17 h / -30 °C

With pyridine; N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; sodium hydride; toluene-4-sulfonic acid; ethylene glycol; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetone;

DOI:10.1021/ja9810639

upstream raw materials:

p-methoxybenzyl chloride

(3aR,6R,7S,7aS)-2,2-Dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

Downstream raw materials:

(3R,4R,5S,6R)-5-(4-Methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-3,4-diol

(2R,3S,4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-phenylsulfanyl-tetrahydro-pyran

2,2,2-Trichloro-acetimidic acid (2S,3S,4S,5R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl ester

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