1-deoxy-3,5-di-O-benzyl-2-O-(3,3-dimethyl-2-oxobutyl)-1-phenylsulfenyl-D-xylofuranose

Base Information

• Chemical Name: 1-deoxy-3,5-di-O-benzyl-2-O-(3,3-dimethyl-2-oxobutyl)-1-phenylsulfenyl-D-xylofuranose
• CAS No.: 192565-69-8
• Molecular Formula: C₃₁H₃₆O₅S
• Molecular Weight: 520.69

Synonyms:1-deoxy-3,5-di-O-benzyl-2-O-(3,3-dimethyl-2-oxobutyl)-1-phenylsulfenyl-D-xylofuranose

Chemical Property of 1-deoxy-3,5-di-O-benzyl-2-O-(3,3-dimethyl-2-oxobutyl)-1-phenylsulfenyl-D-xylofuranose

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Technology Process of 1-deoxy-3,5-di-O-benzyl-2-O-(3,3-dimethyl-2-oxobutyl)-1-phenylsulfenyl-D-xylofuranose

There total 7 articles about 1-deoxy-3,5-di-O-benzyl-2-O-(3,3-dimethyl-2-oxobutyl)-1-phenylsulfenyl-D-xylofuranose 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: 88.0%

1-Bromopinacolon (5469-26-1) + 1-deoxy-3,5-di-O-benzyl-1-phenylsulfenyl-D-xylofuranose (260403-42-7) → 1-deoxy-3,5-di-O-benzyl-2-O-(3,3-dimethyl-2-oxobutyl)-1-phenylsulfenyl-D-xylofuranose (192565-69-8)

Guidance literature:

With sodium hydroxide; Aliquat 336; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/S0040-4020(99)00959-X

Reference yield:

3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose (41341-99-5) → 1-deoxy-3,5-di-O-benzyl-2-O-(3,3-dimethyl-2-oxobutyl)-1-phenylsulfenyl-D-xylofuranose (192565-69-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.08 g / conc. H₂SO₄ / acetonitrile; H₂O / 35 °C

2: 1.049 g / Bu₃P / CH₂Cl₂ / 15.5 h / 0 - 20 °C

3: 88 percent / Aliquat 336; aq. NaOH / CH₂Cl₂ / 1 h / 20 °C

With sodium hydroxide; tributylphosphine; sulfuric acid; Aliquat 336; In dichloromethane; water; acetonitrile; 1: Hydrolysis / 2: Substitution / 3: Etherification;

DOI:10.1016/S0040-4020(99)00959-X

Reference yield:

3,5-di-O-benzyl-D-xylofuranose (16054-77-6,120693-82-5,120693-83-6) → 1-deoxy-3,5-di-O-benzyl-2-O-(3,3-dimethyl-2-oxobutyl)-1-phenylsulfenyl-D-xylofuranose (192565-69-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.049 g / Bu₃P / CH₂Cl₂ / 15.5 h / 0 - 20 °C

2: 88 percent / Aliquat 336; aq. NaOH / CH₂Cl₂ / 1 h / 20 °C

With sodium hydroxide; tributylphosphine; Aliquat 336; In dichloromethane; 1: Substitution / 2: Etherification;

DOI:10.1016/S0040-4020(99)00959-X

upstream raw materials:

1-Bromopinacolon

1-deoxy-3,5-di-O-benzyl-1-phenylsulfenyl-D-xylofuranose

3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

3,5-di-O-benzyl-D-xylofuranose

Downstream raw materials:

{1-[1-((3R,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-furan-3-yloxy)-meth-(Z)-ylidene]-2,2-dimethyl-propoxy}-tert-butyl-dimethyl-silane

1-deoxy-3,5-di-O-benzyl-2-O-(3,3-dimethyl-2-oxobutyl)-1-phenylsulfonyl-D-xylofuranose

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