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

Base Information

• Chemical Name: (3R,4R,5S,6R)-5-(4-Methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-3,4-diol
• CAS No.: 201142-49-6
• Molecular Formula: C₁₉H₂₂O₅S
• Molecular Weight: 362.447
• Mol file: 201142-49-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (3R,4R,5S,6R)-5-(4-Methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-3,4-diol 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: 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:

p-methoxybenzyl chloride (824-94-2) → (3R,4R,5S,6R)-5-(4-Methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-3,4-diol (201142-49-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, 2 h

2: 84 percent / TsOH*H₂O, ethanediol / methanol / 6 h / 25 °C

With sodium hydride; toluene-4-sulfonic acid; ethylene glycol; In methanol;

DOI:10.1021/ja9810639

Reference yield:

(3aR,6R,7S,7aS)-2,2-Dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol (193359-93-2) → (3R,4R,5S,6R)-5-(4-Methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-3,4-diol (201142-49-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, 2 h

2: 84 percent / TsOH*H₂O, ethanediol / methanol / 6 h / 25 °C

With sodium hydride; toluene-4-sulfonic acid; ethylene glycol; In methanol;

DOI:10.1021/ja9810639

upstream raw materials:

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

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:

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

(Z)-2-[(2S,3S,4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxymethyl]-3-[(1S,2R,6R)-6-isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enyl]-propenal

(Z)-2-[(2R,3S,4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxymethyl]-3-[(1S,2R,6R)-6-isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enyl]-propenal

C₅₇H₁₀₀O₉Si₄