(2R,3S,4R)-3-hydroxy-2-phenoxythiocarbonyloxy-5-trityloxy-4-pentanolide

Base Information

• Chemical Name: (2R,3S,4R)-3-hydroxy-2-phenoxythiocarbonyloxy-5-trityloxy-4-pentanolide
• CAS No.: 302605-66-9
• Molecular Formula: C₃₁H₂₆O₆S
• Molecular Weight: 526.61
• Mol file: 302605-66-9.mol

Synonyms:(2R,3S,4R)-3-hydroxy-2-phenoxythiocarbonyloxy-5-trityloxy-4-pentanolide

Chemical Property of (2R,3S,4R)-3-hydroxy-2-phenoxythiocarbonyloxy-5-trityloxy-4-pentanolide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R)-3-hydroxy-2-phenoxythiocarbonyloxy-5-trityloxy-4-pentanolide

There total 4 articles about (2R,3S,4R)-3-hydroxy-2-phenoxythiocarbonyloxy-5-trityloxy-4-pentanolide 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: 87.0%

phenylcarbonochloridothioate (1005-56-7) + (2R,3R,4R)-2,3-dihydroxy-5-trityloxy-4-pentanolide (282101-72-8) → (2R,3S,4R)-3-hydroxy-2-phenoxythiocarbonyloxy-5-trityloxy-4-pentanolide (302605-66-9)

Guidance literature:

With dmap; In acetonitrile; at -10 ℃; for 1h;

DOI:10.1271/bbb.64.1563

Reference yield:

D-xylose (58-86-6) → (2R,3S,4R)-3-hydroxy-2-phenoxythiocarbonyloxy-5-trityloxy-4-pentanolide (302605-66-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 48 percent / 4-(dimethylamino)pyridine / pyridine / 2 h / 60 °C

2: 85 percent / NaHCO₃; Br₂ / ethanol; H₂O / 16 h / 20 °C

3: 87 percent / 4-(dimethylamino)pyridine / acetonitrile / 1 h / -10 °C

With dmap; bromine; sodium hydrogencarbonate; In pyridine; ethanol; water; acetonitrile; 1: Cyclocondensation / 2: Oxidation / 3: Condensation;

DOI:10.1271/bbb.64.1563

Reference yield:

(3R,4R,5R)-5-((trityloxy)methyl)tetrahydrofuran-2,3,4-triol (55726-00-6,72521-12-1,72521-13-2,72521-20-1,72521-21-2,72521-22-3,131285-09-1,131285-24-0) → (2R,3S,4R)-3-hydroxy-2-phenoxythiocarbonyloxy-5-trityloxy-4-pentanolide (302605-66-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / NaHCO₃; Br₂ / ethanol; H₂O / 16 h / 20 °C

2: 87 percent / 4-(dimethylamino)pyridine / acetonitrile / 1 h / -10 °C

With dmap; bromine; sodium hydrogencarbonate; In ethanol; water; acetonitrile; 1: Oxidation / 2: Condensation;

DOI:10.1271/bbb.64.1563

upstream raw materials:

phenylcarbonochloridothioate

(2R,3R,4R)-2,3-dihydroxy-5-trityloxy-4-pentanolide

D-xylose

(3R,4R,5R)-5-((trityloxy)methyl)tetrahydrofuran-2,3,4-triol

Downstream raw materials:

(2R,3R,4R,5R)-3,5-bis(methoxymethoxy)-5-(3,4-methylenedioxyphenyl)-4-pivaloyloxymethyl-1-trityloxy-2-pentanol

(2R,3R,4R,5S)-3,5-bis(methoxymethoxy)-5-(3,4-methylenedioxyphenyl)-4-pivaloyloxymethyl-1-trityloxy-2-pentanol

(3R,4R,5R)-3-((R)-Benzo[1,3]dioxol-5-yl-methoxymethoxy-methyl)-4-methoxymethoxy-5-trityloxymethyl-dihydro-furan-2-one

(3R,4R,5R)-4-methoxymethoxy-3-[(1S)-1-methoxymethoxy-1-(3,4-methylenedioxyphenyl)methyl]-5-trityloxymethyldihydro-2(3H)-furanone