Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yl ester
• CAS No.: 120316-51-0
• Molecular Formula: C₂₈H₃₀O₅Se
• Molecular Weight: 525.503
• Mol file: 120316-51-0.mol

Synonyms:Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yl ester

Chemical Property of Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yl ester

There total 1 articles about Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yl ester 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:

Phenylselenyl chloride (5707-04-0) + silver(I) acetate (563-63-3) + 1,5-anhydro-3,4-di-O-benzyl-2,6-dideoxy-D-arabino-hex-1-enitol (111002-90-5) → Acetic acid (2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yl ester (120316-48-5) + Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yl ester (120316-51-0)

Guidance literature:

Product distribution; multistep reaction;

DOI:10.1016/S0040-4020(97)00571-1

Reference yield:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) + Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yl ester (120316-51-0) → C54H58O9Se (120316-60-1) + C54H58O9Se (120316-64-5)

Guidance literature:

With 4 A molecular sieve; trimethylsilyl trifluoromethanesulfonate; In diethyl ether; at 0 ℃; for 0.5h; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4039(01)80327-0

Reference yield:

Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yl ester (120316-51-0) → methyl 2,3,4-tri-O-benzyl-6-O-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-α-D-glucopyranoside (120316-65-6)

Guidance literature:

Multi-step reaction with 2 steps

1: molecular sieves 4A / TMSOTf / diethyl ether / 0.5 h / 0 °C

2: Ph₃SnH / toluene / Heating

With 4 A molecular sieve; triphenylstannane; trimethylsilyl trifluoromethanesulfonate; In diethyl ether; toluene;

DOI:10.1016/S0040-4039(01)80327-0

upstream raw materials:

Phenylselenyl chloride

silver(I) acetate

1,5-anhydro-3,4-di-O-benzyl-2,6-dideoxy-D-arabino-hex-1-enitol

Downstream raw materials:

C₅₄H₅₈O₉Se

C₅₄H₅₈O₉Se

methyl 2,3,4-tri-O-benzyl-6-O-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-α-D-glucopyranoside