(2R,4R,4aS,7R,7aS)-7-Hydroxy-2-phenyl-4-trityloxymethyl-tetrahydro-furo[3,2-d][1,3]dioxin-6-one

Base Information

• Chemical Name: (2R,4R,4aS,7R,7aS)-7-Hydroxy-2-phenyl-4-trityloxymethyl-tetrahydro-furo[3,2-d][1,3]dioxin-6-one
• CAS No.: 201995-64-4
• Molecular Formula: C₃₂H₂₈O₆
• Molecular Weight: 508.571
• Mol file: 201995-64-4.mol

Synonyms:

Chemical Property of (2R,4R,4aS,7R,7aS)-7-Hydroxy-2-phenyl-4-trityloxymethyl-tetrahydro-furo[3,2-d][1,3]dioxin-6-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4R,4aS,7R,7aS)-7-Hydroxy-2-phenyl-4-trityloxymethyl-tetrahydro-furo[3,2-d][1,3]dioxin-6-one

There total 1 articles about (2R,4R,4aS,7R,7aS)-7-Hydroxy-2-phenyl-4-trityloxymethyl-tetrahydro-furo[3,2-d][1,3]dioxin-6-one 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:

trityl chloride (76-83-5) + 3,5-O-benzylidene-D-gulonolactone (201995-63-3) → (2R,4R,4aS,7R,7aS)-7-Hydroxy-2-phenyl-4-trityloxymethyl-tetrahydro-furo[3,2-d][1,3]dioxin-6-one (201995-64-4)

Guidance literature:

With dmap; triethylamine;

DOI:10.1016/S0040-4039(97)10533-0

Reference yield:

(2R,4R,4aS,7R,7aS)-7-Hydroxy-2-phenyl-4-trityloxymethyl-tetrahydro-furo[3,2-d][1,3]dioxin-6-one (201995-64-4) → (4S,5R,6S,8R)-4,6-Dimethoxy-2,8-dimethyl-5-trimethylsilanyloxy-nonanedioic acid benzyl ester tert-butyl ester (201995-77-9)

Guidance literature:

Multi-step reaction with 9 steps

1: Al(CH₃)3 / toluene / 0 °C

2: Ag₂O / dimethylformamide; CH₂Cl₂

3: LiHAl(OEt)3 / tetrahydrofuran / 0 °C

5: TFA / methanol

6: 1.) H₂; 2.) NaIO₄, NaHCO₃ / 1.) Pd(OH)2 / 1.) EtOH, EtOAc

8: H₂, HClO₄ /

9: DMAP

With dmap; sodium periodate; perchloric acid; hydrogen; trimethylaluminum; sodium hydrogencarbonate; lithium triethoxyaluminum hydride; trifluoroacetic acid; silver(l) oxide; palladium dihydroxide; ; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(97)10533-0

Reference yield:

(2R,4R,4aS,7R,7aS)-7-Hydroxy-2-phenyl-4-trityloxymethyl-tetrahydro-furo[3,2-d][1,3]dioxin-6-one (201995-64-4) → (4S,5R,6S,8R)-9-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4,6-dimethoxy-2,8-dimethyl-nonanoic acid methyl ester

Guidance literature:

Multi-step reaction with 14 steps

1: Al(CH₃)3 / toluene / 0 °C

2: Ag₂O / dimethylformamide; CH₂Cl₂

3: LiHAl(OEt)3 / tetrahydrofuran / 0 °C

5: TFA / methanol

6: 1.) H₂; 2.) NaIO₄, NaHCO₃ / 1.) Pd(OH)2 / 1.) EtOH, EtOAc

8: H₂, HClO₄ /

9: DMAP

10: H₂ / Pd/C

11: BH₃-S(CH₃)2

12: HCl / diethyl ether; benzene

13: DMAP

With hydrogenchloride; dmap; sodium periodate; perchloric acid; dimethylsulfide borane complex; hydrogen; trimethylaluminum; sodium hydrogencarbonate; lithium triethoxyaluminum hydride; trifluoroacetic acid; silver(l) oxide; palladium dihydroxide; palladium on activated charcoal; ; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1016/S0040-4039(97)10533-0

upstream raw materials:

trityl chloride

3,5-O-benzylidene-D-gulonolactone

Downstream raw materials:

(R)-2-Hydroxy-2-((2R,4R,5S,6R)-5-hydroxy-2-phenyl-6-trityloxymethyl-[1,3]dioxan-4-yl)-N-methoxy-N-methyl-acetamide

(4S,5R,6S,8R)-5-Hydroxy-4,6-dimethoxy-2,8-dimethyl-nonanedioic acid benzyl ester tert-butyl ester

(4S,5R,6S,8R)-4,6-Dimethoxy-2,8-dimethyl-5-trimethylsilanyloxy-nonanedioic acid benzyl ester tert-butyl ester

(4S,5R,6S,8R)-9-(tert-Butyl-diphenyl-silanyloxy)-4,6-dimethoxy-2,8-dimethyl-5-trimethylsilanyloxy-nonanoic acid methyl ester