[(2S,4aR,5S,6R,8R,8aS)-6-Methoxy-2-phenyl-5-(toluene-4-sulfonyl)-hexahydro-pyrano[3,4-d][1,3]dioxin-8-yl]-methanol

Base Information

• Chemical Name: [(2S,4aR,5S,6R,8R,8aS)-6-Methoxy-2-phenyl-5-(toluene-4-sulfonyl)-hexahydro-pyrano[3,4-d][1,3]dioxin-8-yl]-methanol
• CAS No.: 502635-97-4
• Molecular Formula: C₂₂H₂₆O₇S
• Molecular Weight: 434.51
• Mol file: 502635-97-4.mol

Synonyms:[(2S,4aR,5S,6R,8R,8aS)-6-Methoxy-2-phenyl-5-(toluene-4-sulfonyl)-hexahydro-pyrano[3,4-d][1,3]dioxin-8-yl]-methanol

Chemical Property of [(2S,4aR,5S,6R,8R,8aS)-6-Methoxy-2-phenyl-5-(toluene-4-sulfonyl)-hexahydro-pyrano[3,4-d][1,3]dioxin-8-yl]-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2S,4aR,5S,6R,8R,8aS)-6-Methoxy-2-phenyl-5-(toluene-4-sulfonyl)-hexahydro-pyrano[3,4-d][1,3]dioxin-8-yl]-methanol

There total 5 articles about [(2S,4aR,5S,6R,8R,8aS)-6-Methoxy-2-phenyl-5-(toluene-4-sulfonyl)-hexahydro-pyrano[3,4-d][1,3]dioxin-8-yl]-methanol 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: 89.0%

benzaldehyde dimethyl acetal (1125-88-8) + methyl 2,3-dideoxy-2,3-C-hydroxymethyl-2-C-p-tolylsulfonyl-β-D-altropyranoside (502635-93-0) → [(2S,4aR,5S,6R,8R,8aS)-6-Methoxy-2-phenyl-5-(toluene-4-sulfonyl)-hexahydro-pyrano[3,4-d][1,3]dioxin-8-yl]-methanol (502635-97-4)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 60 ℃; pH=2;

DOI:10.1016/S0008-6215(02)00231-8

Reference yield:

[(2R,4aR,6R,7S,8R,8aS)-6-Methoxy-2-phenyl-7-(toluene-4-sulfonyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl]-methanol (502635-87-2) → [(2S,4aR,5S,6R,8R,8aS)-6-Methoxy-2-phenyl-5-(toluene-4-sulfonyl)-hexahydro-pyrano[3,4-d][1,3]dioxin-8-yl]-methanol (502635-97-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / AcOH; water / 2 h / 80 °C

2: 89 percent / TsOH / dimethylformamide / 60 °C / pH 2

With water; toluene-4-sulfonic acid; acetic acid; In N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(02)00231-8

Reference yield:

[(2R,4aR,6R,7R,8R,8aS)-6-Methoxy-2-phenyl-7-(toluene-4-sulfonyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl]-methanol (502635-85-0) → [(2S,4aR,5S,6R,8R,8aS)-6-Methoxy-2-phenyl-5-(toluene-4-sulfonyl)-hexahydro-pyrano[3,4-d][1,3]dioxin-8-yl]-methanol (502635-97-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 67 percent / DBU; oxolane / 168000 h / 20 °C

2: 84 percent / AcOH; water / 2 h / 80 °C

3: 89 percent / TsOH / dimethylformamide / 60 °C / pH 2

With tetrahydrofuran; water; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(02)00231-8

upstream raw materials:

benzaldehyde dimethyl acetal

methyl 2,3-dideoxy-2,3-C-hydroxymethyl-2-C-p-tolylsulfonyl-β-D-altropyranoside

[(2R,4aR,6R,7S,8R,8aS)-6-Methoxy-2-phenyl-7-(toluene-4-sulfonyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl]-methanol

[(2R,4aR,6R,7R,8R,8aS)-6-Methoxy-2-phenyl-7-(toluene-4-sulfonyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl]-methanol

Downstream raw materials:

Acetic acid (2S,4aR,5S,6R,8R,8aS)-6-methoxy-2-phenyl-5-(toluene-4-sulfonyl)-hexahydro-pyrano[3,4-d][1,3]dioxin-8-ylmethyl ester