4,5-anhydro-1-O-benzyl-2-deoxy-3-O-(methoxymethyl)-D-threo-pentitol

Base Information

• Chemical Name: 4,5-anhydro-1-O-benzyl-2-deoxy-3-O-(methoxymethyl)-D-threo-pentitol
• CAS No.: 264872-35-7
• Molecular Formula: C₁₄H₂₀O₄
• Molecular Weight: 252.31
• Mol file: 264872-35-7.mol

Synonyms:4,5-anhydro-1-O-benzyl-2-deoxy-3-O-(methoxymethyl)-D-threo-pentitol

Chemical Property of 4,5-anhydro-1-O-benzyl-2-deoxy-3-O-(methoxymethyl)-D-threo-pentitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,5-anhydro-1-O-benzyl-2-deoxy-3-O-(methoxymethyl)-D-threo-pentitol

There total 3 articles about 4,5-anhydro-1-O-benzyl-2-deoxy-3-O-(methoxymethyl)-D-threo-pentitol 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%

chloromethyl methyl ether (107-30-2) + 4,5-anhydro-1-O-benzyl-2-deoxy-D-threo-pentitol (264872-34-6) → 4,5-anhydro-1-O-benzyl-2-deoxy-3-O-(methoxymethyl)-D-threo-pentitol (264872-35-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/S0040-4020(99)01052-2

Reference yield:

(E)-(((5-chloropent-3-en-1-yl)oxy)methyl)benzene (264872-32-4) → 4,5-anhydro-1-O-benzyl-2-deoxy-3-O-(methoxymethyl)-D-threo-pentitol (264872-35-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / (DHQD)2PHAL; K₂OsO₂(OH)4; K₃[F₃(CN)6] / 2-methyl-propan-2-ol; H₂O / 24 h / 0 °C

2: 89 percent / NaOH / tetrahydrofuran / 2 h / 0 °C

3: 89 percent / iPr₂NEt / CH₂Cl₂ / 0 - 20 °C

With sodium hydroxide; potassium dioxotetrahydroxoosmate(VI); 1,4-bis(9-O-dihydroquinidine)phthalazine; N-ethyl-N,N-diisopropylamine; potassium hexacyanoferrate(III); In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; 1: Sharpless asymmetric dihydroxylation / 2: Cyclization / 3: Etherification;

DOI:10.1016/S0040-4020(99)01052-2

Reference yield:

5-O-benzyl-1-chloro-1,4-dideoxy-D-threo-pentitol (264872-33-5) → 4,5-anhydro-1-O-benzyl-2-deoxy-3-O-(methoxymethyl)-D-threo-pentitol (264872-35-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / NaOH / tetrahydrofuran / 2 h / 0 °C

2: 89 percent / iPr₂NEt / CH₂Cl₂ / 0 - 20 °C

With sodium hydroxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1: Cyclization / 2: Etherification;

DOI:10.1016/S0040-4020(99)01052-2

upstream raw materials:

chloromethyl methyl ether

4,5-anhydro-1-O-benzyl-2-deoxy-D-threo-pentitol

(E)-(((5-chloropent-3-en-1-yl)oxy)methyl)benzene

5-O-benzyl-1-chloro-1,4-dideoxy-D-threo-pentitol

Downstream raw materials:

5-O-benzyl-2-[(tert-butoxycarbonyl)(methyl)amino]-1,2,4-trideoxy-3-O-(methoxymethyl)-1-phenyl-D-threo-pentitol

5-O-benzyl-2-[(tert-butoxycarbonyl)amino]-1,2,4-trideoxy-3-O-(methoxymethyl)-1-phenyl-D-threo-pentitol

2-amino-5-O-benzyl-1,2,4-trideoxy-3-O-(methoxymethyl)-1-phenyl-D-threo-pentitol

C₂₀H₂₄O₃