(R)-1-O-Benzyl-5-ethylenedithio-1,2-decandiol

Base Information

• Chemical Name: (R)-1-O-Benzyl-5-ethylenedithio-1,2-decandiol
• CAS No.: 381719-04-6
• Molecular Formula: C₁₉H₃₀O₂S₂
• Molecular Weight: 354.578
• Mol file: 381719-04-6.mol

Synonyms:(R)-1-O-Benzyl-5-ethylenedithio-1,2-decandiol

Chemical Property of (R)-1-O-Benzyl-5-ethylenedithio-1,2-decandiol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-O-Benzyl-5-ethylenedithio-1,2-decandiol

There total 10 articles about (R)-1-O-Benzyl-5-ethylenedithio-1,2-decandiol 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: 73.0%

ethane-1,2-dithiol (540-63-6) + 1-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-decan-5-one (381719-01-3) → (R)-1-O-Benzyl-5-ethylenedithio-1,2-decandiol (381719-04-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1055/s-2001-16789

Reference yield:

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone (52813-63-5) → (R)-1-O-Benzyl-5-ethylenedithio-1,2-decandiol (381719-04-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 70 percent / CF₃SO₃H / CH₂Cl₂; hexane / 0.5 h / 0 °C

2: aq. NaOH / 1 h / 20 °C

3: TBABr / acetone / 8 h / 20 °C

4: imidazole / tetrahydrofuran / 15 h / 20 °C

5: LiAlH₄ / tetrahydrofuran / 4 h / 20 °C

6: PCC; AcONa / CH₂Cl₂ / 1 h / 20 °C

7: 90 percent / diethyl ether / 4 h / 20 °C

8: 88 percent / PCC; AcONa / CH₂Cl₂ / 1 h / 20 °C

9: 73 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.5 h / 20 °C

With 1H-imidazole; sodium hydroxide; lithium aluminium tetrahydride; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; tetrabutylammomium bromide; sodium acetate; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetone;

DOI:10.1055/s-2001-16789

Reference yield:

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) → (R)-1-O-Benzyl-5-ethylenedithio-1,2-decandiol (381719-04-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 70 percent / CF₃SO₃H / CH₂Cl₂; hexane / 0.5 h / 0 °C

2: aq. NaOH / 1 h / 20 °C

3: TBABr / acetone / 8 h / 20 °C

4: imidazole / tetrahydrofuran / 15 h / 20 °C

5: LiAlH₄ / tetrahydrofuran / 4 h / 20 °C

6: PCC; AcONa / CH₂Cl₂ / 1 h / 20 °C

7: 90 percent / diethyl ether / 4 h / 20 °C

8: 88 percent / PCC; AcONa / CH₂Cl₂ / 1 h / 20 °C

9: 73 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.5 h / 20 °C

With 1H-imidazole; sodium hydroxide; lithium aluminium tetrahydride; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; tetrabutylammomium bromide; sodium acetate; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetone;

DOI:10.1055/s-2001-16789

upstream raw materials:

ethane-1,2-dithiol

1-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-decan-5-one

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

O-benzyl 2,2,2-trichloroacetimidate

Downstream raw materials:

(R)-1-O-Benzyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-ethylenedithio-1,2-decandiol

(R)-1-O-Benzyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-5-ethylenedithio-1,2-decandiol