(2R,3R,4S,5S)-4-Azido-2-((R)-1-benzyloxy-2,2-bis-phenylsulfanyl-ethyl)-5-methoxy-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (2R,3R,4S,5S)-4-Azido-2-((R)-1-benzyloxy-2,2-bis-phenylsulfanyl-ethyl)-5-methoxy-tetrahydro-pyran-3-ol
• CAS No.: 864941-79-7
• Molecular Formula: C₂₇H₂₉N₃O₄S₂
• Molecular Weight: 523.677
• Mol file: 864941-79-7.mol

Synonyms:(2R,3R,4S,5S)-4-Azido-2-((R)-1-benzyloxy-2,2-bis-phenylsulfanyl-ethyl)-5-methoxy-tetrahydro-pyran-3-ol

Chemical Property of (2R,3R,4S,5S)-4-Azido-2-((R)-1-benzyloxy-2,2-bis-phenylsulfanyl-ethyl)-5-methoxy-tetrahydro-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5S)-4-Azido-2-((R)-1-benzyloxy-2,2-bis-phenylsulfanyl-ethyl)-5-methoxy-tetrahydro-pyran-3-ol

There total 12 articles about (2R,3R,4S,5S)-4-Azido-2-((R)-1-benzyloxy-2,2-bis-phenylsulfanyl-ethyl)-5-methoxy-tetrahydro-pyran-3-ol 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: 91.0%

(2R,3R,3aR,6S,7R,7aR)-7-azido-3-benzyloxy-2,6-dimethoxy-hexahydrofuro[3,2-b]pyran (828914-51-8) + thiophenol (108-98-5) → (2R,3R,4S,5S)-4-Azido-2-((R)-1-benzyloxy-2,2-bis-phenylsulfanyl-ethyl)-5-methoxy-tetrahydro-pyran-3-ol (864941-79-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 3.5h;

DOI:10.1021/jo050727b

Reference yield:

(3R,4S,5R)-2-Methoxy-5-vinyl-tetrahydro-furan-3,4-diol → (2R,3R,4S,5S)-4-Azido-2-((R)-1-benzyloxy-2,2-bis-phenylsulfanyl-ethyl)-5-methoxy-tetrahydro-pyran-3-ol (864941-79-7)

Guidance literature:

Multi-step reaction with 10 steps

1: 58 percent / dibutyltin oxide; n-Bu₄NI; molecular sieves 4 Angstroem / acetonitrile / 5 h / Heating

2: 91 percent / NaH / dimethylformamide; various solvent(s) / 0 - 20 °C

3: 68 percent / Cl₂Ru(=CHPh)(PCy₃)2 / CH₂Cl₂ / 8 h / Heating

4: N-bromosuccinimide / tetrahydrofuran; H₂O / 1.5 h / 20 °C

5: sodium hydroxide / tetrahydrofuran / 1 h / Heating

6: 300 mg / sodium azide / 2-methoxy-ethanol / 2 h / 126 °C

7: Dess-Martin periodinane / CH₂Cl₂ / 2.5 h / 20 °C

8: NaBH₄ / methanol / 1 h / 0 °C

9: 253 mg / NaH / dimethylformamide; various solvent(s) / 0 - 20 °C

10: 91 percent / BF₃*Et₂O / CH₂Cl₂ / 3.5 h / -78 °C

With sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; Grubbs catalyst first generation; sodium azide; 4 A molecular sieve; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; Dess-Martin periodane; In tetrahydrofuran; methanol; dichloromethane; 2-methoxy-ethanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo050727b

Reference yield:

methyl 3-O-allyl-5,6-dideoxy-β-D-ribo-hex-5-enofuranoside (828914-43-8) → (2R,3R,4S,5S)-4-Azido-2-((R)-1-benzyloxy-2,2-bis-phenylsulfanyl-ethyl)-5-methoxy-tetrahydro-pyran-3-ol (864941-79-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 91 percent / NaH / dimethylformamide; various solvent(s) / 0 - 20 °C

2: 68 percent / Cl₂Ru(=CHPh)(PCy₃)2 / CH₂Cl₂ / 8 h / Heating

3: N-bromosuccinimide / tetrahydrofuran; H₂O / 1.5 h / 20 °C

4: sodium hydroxide / tetrahydrofuran / 1 h / Heating

5: 300 mg / sodium azide / 2-methoxy-ethanol / 2 h / 126 °C

6: Dess-Martin periodinane / CH₂Cl₂ / 2.5 h / 20 °C

7: NaBH₄ / methanol / 1 h / 0 °C

8: 253 mg / NaH / dimethylformamide; various solvent(s) / 0 - 20 °C

9: 91 percent / BF₃*Et₂O / CH₂Cl₂ / 3.5 h / -78 °C

With sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; Grubbs catalyst first generation; sodium azide; boron trifluoride diethyl etherate; sodium hydride; Dess-Martin periodane; In tetrahydrofuran; methanol; dichloromethane; 2-methoxy-ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jo050727b

upstream raw materials:

(2R,3R,3aR,6S,7R,7aR)-7-azido-3-benzyloxy-2,6-dimethoxy-hexahydrofuro[3,2-b]pyran

thiophenol

methyl 3-O-allyl-5,6-dideoxy-β-D-ribo-hex-5-enofuranoside

(2R,3R,3aR,7aR)-3-benzyloxy-2-methoxy-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran

Refernces