(2R,3S,4R,1'R,2'S)-2',3,4-Tris(benzyloxy)-2-<1'-<(methylsulfonyl)oxy>-4'-phthalimidobutyl>tetrahydrofuran

Base Information

• Chemical Name: (2R,3S,4R,1'R,2'S)-2',3,4-Tris(benzyloxy)-2-<1'-<(methylsulfonyl)oxy>-4'-phthalimidobutyl>tetrahydrofuran
• CAS No.: 140201-69-0
• Molecular Formula: C₃₈H₃₉NO₉S
• Molecular Weight: 685.795
• Mol file: 140201-69-0.mol

Synonyms:(2R,3S,4R,1'R,2'S)-2',3,4-Tris(benzyloxy)-2-<1'-<(methylsulfonyl)oxy>-4'-phthalimidobutyl>tetrahydrofuran

Chemical Property of (2R,3S,4R,1'R,2'S)-2',3,4-Tris(benzyloxy)-2-<1'-<(methylsulfonyl)oxy>-4'-phthalimidobutyl>tetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R,1'R,2'S)-2',3,4-Tris(benzyloxy)-2-<1'-<(methylsulfonyl)oxy>-4'-phthalimidobutyl>tetrahydrofuran

There total 11 articles about (2R,3S,4R,1'R,2'S)-2',3,4-Tris(benzyloxy)-2-<1'-<(methylsulfonyl)oxy>-4'-phthalimidobutyl>tetrahydrofuran 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%

methanesulfonyl chloride (124-63-0) + (2R,3S,4S,5R,6S)-2,3,4,6-Tetra-O-benzyl-1,2,3,4,5,6-hexahydroxy-8-N-phthaloyloctan-8-amine (140386-73-8) → (2R,3S,4R,1'R,2'S)-2',3,4-Tris(benzyloxy)-2-<1'-<(methylsulfonyl)oxy>-4'-phthalimidobutyl>tetrahydrofuran (140201-69-0)

Guidance literature:

With pyridine; dmap; 0 deg C to r.t.;

DOI:10.1016/S0040-4039(00)92514-0

Reference yield:

phthalimide (136918-14-4,85-41-6) → (2R,3S,4R,1'R,2'S)-2',3,4-Tris(benzyloxy)-2-<1'-<(methylsulfonyl)oxy>-4'-phthalimidobutyl>tetrahydrofuran (140201-69-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / PPh₃, DEAD / tetrahydrofuran / a) 0 deg C to r.t., b) r.t., 24 h

2: 92 percent / 25percent HCl / methanol / 2 h / 60 °C

3: 89 percent / DMAP / CH₂Cl₂ / 1 h / -30 °C

With hydrogenchloride; dmap; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo00037a043

Reference yield:

2,3,4-tri-O-benzyl-D-xylopyranose (18039-26-4,20787-16-0,20787-21-7,77943-32-9,77943-33-0,89615-43-0,89615-44-1,90899-55-1) → (2R,3S,4R,1'R,2'S)-2',3,4-Tris(benzyloxy)-2-<1'-<(methylsulfonyl)oxy>-4'-phthalimidobutyl>tetrahydrofuran (140201-69-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 94 percent / tetrahydrofuran / 48 h / Ambient temperature

2: 82 percent / N-ethyldiisopropylamine / CH₂Cl₂ / 24 h

3: 1.) ozone, 2.) PPh₃ / 1.) CH₂Cl₂, 2.) a) -78 deg C, 1 h, b) r.t., 2h

4: 9 percent / CrCl₃, LiAlH₄ / tetrahydrofuran / 60 h / -6.5 °C

5: 1. NaH / 1.) DMF, 2.) DMF, r.t., 24 h

6: 1.) ozone, 2.) PPh₃ / 1.) CH₂Cl₂

7: LiAlH₄ / diethyl ether / 24 h / 0 deg C to r.t.

8: 93 percent / PPh₃, DEAD / tetrahydrofuran / a) 0 deg C to r.t., b) r.t., 24 h

9: 92 percent / 25percent HCl / methanol / 2 h / 60 °C

10: 89 percent / DMAP / CH₂Cl₂ / 1 h / -30 °C

With hydrogenchloride; dmap; chromium chloride; lithium aluminium tetrahydride; sodium hydride; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1021/jo00037a043

upstream raw materials:

methanesulfonyl chloride

(2R,3S,4S,5R,6S)-2,3,4,6-Tetra-O-benzyl-1,2,3,4,5,6-hexahydroxy-8-N-phthaloyloctan-8-amine

phthalimide

2,3,4-tri-O-benzyl-D-xylopyranose