(2S,3S,4S,5R)-5-[1,3]Dithian-2-yl-4-(4-methoxy-benzyloxy)-3-methyl-hexane-1,2-diol

Base Information

• Chemical Name: (2S,3S,4S,5R)-5-[1,3]Dithian-2-yl-4-(4-methoxy-benzyloxy)-3-methyl-hexane-1,2-diol
• CAS No.: 114114-37-3
• Molecular Formula: C₁₉H₃₀O₄S₂
• Molecular Weight: 386.577
• Mol file: 114114-37-3.mol

Synonyms:(2S,3S,4S,5R)-5-[1,3]Dithian-2-yl-4-(4-methoxy-benzyloxy)-3-methyl-hexane-1,2-diol

Chemical Property of (2S,3S,4S,5R)-5-[1,3]Dithian-2-yl-4-(4-methoxy-benzyloxy)-3-methyl-hexane-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S,5R)-5-[1,3]Dithian-2-yl-4-(4-methoxy-benzyloxy)-3-methyl-hexane-1,2-diol

There total 5 articles about (2S,3S,4S,5R)-5-[1,3]Dithian-2-yl-4-(4-methoxy-benzyloxy)-3-methyl-hexane-1,2-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: 75.0%

(S)-4-[(1R,2S,3R)-3-[1,3]Dithian-2-yl-2-(4-methoxy-benzyloxy)-1-methyl-butyl]-2,2-dimethyl-[1,3]dioxolane (114130-12-0) → (2S,3S,4S,5R)-5-[1,3]Dithian-2-yl-4-(4-methoxy-benzyloxy)-3-methyl-hexane-1,2-diol (114114-37-3)

Guidance literature:

With acetic acid; at 60 ℃; for 1.5h;

DOI:10.1007/BF00953634

Reference yield:

(2R,3S,4R)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-[1,3]dithian-2-yl-pentan-3-ol (114114-36-2) → (2S,3S,4S,5R)-5-[1,3]Dithian-2-yl-4-(4-methoxy-benzyloxy)-3-methyl-hexane-1,2-diol (114114-37-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) DMF, room temp., 5 min, 2.) DMF, 1 h

2: 75 percent / 80 percent AcOH / 1.5 h / 60 °C

With sodium hydride; acetic acid;

DOI:10.1016/S0040-4020(01)81090-5

Reference yield:

1,6-anhydro-2,4-didesoxy-2,4-di-C-methyl-β-D-galactopyranose (114114-35-1) → (2S,3S,4S,5R)-5-[1,3]Dithian-2-yl-4-(4-methoxy-benzyloxy)-3-methyl-hexane-1,2-diol (114114-37-3)

Guidance literature:

Multi-step reaction with 4 steps

1: BF₃*Et₂O / CH₂Cl₂ / 12 h / Ambient temperature

2: TsOH*H₂O / acetone / 1 h

3: 1.) NaH / 1.) DMF, room temp., 5 min, 2.) DMF, 1 h

4: 75 percent / 80 percent AcOH / 1.5 h / 60 °C

With boron trifluoride diethyl etherate; sodium hydride; toluene-4-sulfonic acid; acetic acid; In dichloromethane; acetone;

DOI:10.1016/S0040-4020(01)81090-5

upstream raw materials:

(S)-4-[(1R,2S,3R)-3-[1,3]Dithian-2-yl-2-(4-methoxy-benzyloxy)-1-methyl-butyl]-2,2-dimethyl-[1,3]dioxolane

(2R,3S,4R)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-[1,3]dithian-2-yl-pentan-3-ol

1,6-anhydro-2,4-didesoxy-2,4-di-C-methyl-β-D-galactopyranose

(2S,3R,4S,5R)-5-[1,3]Dithian-2-yl-3-methyl-hexane-1,2,4-triol

Downstream raw materials:

{(1R,2R)-2-[(4R,5R,6R)-6-[(S)-2-((R)-Benzenesulfinyl)-1-methyl-ethyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-1-ethyl-propoxy}-tert-butyl-diphenyl-silane

{(1R,2R)-2-[(4R,5R,6R)-6-[(S)-2-((S)-Benzenesulfinyl)-1-methyl-ethyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-1-ethyl-propoxy}-tert-butyl-diphenyl-silane

(2S,3R,4S)-3-Benzenesulfinyl-4-[(4R,5R,6R)-6-[(1R,2R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-butyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-pentan-2-ol

(2R,3R,4S)-3-Benzenesulfinyl-4-[(4R,5R,6R)-6-[(1R,2R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-butyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-pentan-2-ol