D-threo-Pentose, 2,5-anhydro-3,4-dideoxy-4-[[(1,1-

Base Information

• Chemical Name: D-threo-Pentose, 2,5-anhydro-3,4-dideoxy-4-[[(1,1-
• CAS No.: 561066-37-3
• Molecular Formula: C₁₀H₁₇NO₄
• Molecular Weight: 215.249
• Mol file: 561066-37-3.mol

Synonyms:D-threo-Pentose, 2,5-anhydro-3,4-dideoxy-4-[[(1,1-

Chemical Property of D-threo-Pentose, 2,5-anhydro-3,4-dideoxy-4-[[(1,1-

Chemical Property:

• PSA: 64.63000
• LogP: 1.25840

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of D-threo-Pentose, 2,5-anhydro-3,4-dideoxy-4-[[(1,1-

There total 8 articles about D-threo-Pentose, 2,5-anhydro-3,4-dideoxy-4-[[(1,1- 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: 51.0%

(2S,4S)-2-(hydroxymethyl)-4-(tert-butoxycarbonylamino)tetrahydrofuran (561066-32-8) → ((3S,5S)-5-Formyl-tetrahydro-furan-3-yl)-carbamic acid tert-butyl ester (561066-37-3)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -70 - 20 ℃; for 1.75h;

DOI:10.1016/S0968-0896(02)00535-7

Reference yield:

1,2-O-isopropylidene-5-O-(4-toluoyl)-D-xylofuranose (75096-60-5) → ((3S,5S)-5-Formyl-tetrahydro-furan-3-yl)-carbamic acid tert-butyl ester (561066-37-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 96 percent / 1,2-dichloro-ethane / 1.5 h / Heating

2.1: 100 percent / Bu₃SnH; AIBN / toluene / 2 h / Heating

3.1: 85 percent / Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 1 h / 0 °C

4.1: diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.17 h / -5 °C

4.2: 100 percent / diphenyl phosphorazidate / tetrahydrofuran / -5 - 20 °C

5.1: 93 percent / hydrogen / Pd/C / ethyl acetate / 20 °C / atmospheric pressure

6.1: 77 percent / MeOH; sodium / 6 h / 20 °C

7.1: 51 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1.75 h / -70 - 20 °C

With methanol; triethylsilane; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; hydrogen; tri-n-butyl-tin hydride; sodium; dimethyl sulfoxide; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; toluene; 2.1: Barton-McCombie reaction / 4.1: Mitsunobu reaction / 4.2: Mitsunobu reaction / 6.1: Zemplen reaction / 7.1: Swern oxidation;

DOI:10.1016/S0968-0896(02)00535-7

Reference yield:

1,2-O-isopropylidene-α-D-xylose (20031-21-4) → ((3S,5S)-5-Formyl-tetrahydro-furan-3-yl)-carbamic acid tert-butyl ester (561066-37-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 95 percent / pyridine

2.1: 96 percent / 1,2-dichloro-ethane / 1.5 h / Heating

3.1: 100 percent / Bu₃SnH; AIBN / toluene / 2 h / Heating

4.1: 85 percent / Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 1 h / 0 °C

5.1: diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.17 h / -5 °C

5.2: 100 percent / diphenyl phosphorazidate / tetrahydrofuran / -5 - 20 °C

6.1: 93 percent / hydrogen / Pd/C / ethyl acetate / 20 °C / atmospheric pressure

7.1: 77 percent / MeOH; sodium / 6 h / 20 °C

8.1: 51 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1.75 h / -70 - 20 °C

With pyridine; methanol; triethylsilane; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; hydrogen; tri-n-butyl-tin hydride; sodium; dimethyl sulfoxide; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; toluene; 3.1: Barton-McCombie reaction / 5.1: Mitsunobu reaction / 5.2: Mitsunobu reaction / 7.1: Zemplen reaction / 8.1: Swern oxidation;

DOI:10.1016/S0968-0896(02)00535-7

upstream raw materials:

(2S,4S)-2-(hydroxymethyl)-4-(tert-butoxycarbonylamino)tetrahydrofuran

1,2-O-isopropylidene-5-O-(4-toluoyl)-D-xylofuranose

1,2-O-isopropylidene-α-D-xylose

3-deoxy-1,2-O-isopropylidene-5-O-(4-methylbenzoyl)-α-D-erythro-pentofuranose