(Z)-(8S,9R)-8,10-Bis-(tert-butyl-diphenyl-silanyloxy)-9-hydroxy-dec-5-enoic acid

Base Information

• Chemical Name: (Z)-(8S,9R)-8,10-Bis-(tert-butyl-diphenyl-silanyloxy)-9-hydroxy-dec-5-enoic acid
• CAS No.: 148903-92-8
• Molecular Formula: C₄₂H₅₄O₅Si₂
• Molecular Weight: 695.059
• Mol file: 148903-92-8.mol

Synonyms:(Z)-(8S,9R)-8,10-Bis-(tert-butyl-diphenyl-silanyloxy)-9-hydroxy-dec-5-enoic acid

Chemical Property of (Z)-(8S,9R)-8,10-Bis-(tert-butyl-diphenyl-silanyloxy)-9-hydroxy-dec-5-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(8S,9R)-8,10-Bis-(tert-butyl-diphenyl-silanyloxy)-9-hydroxy-dec-5-enoic acid

There total 4 articles about (Z)-(8S,9R)-8,10-Bis-(tert-butyl-diphenyl-silanyloxy)-9-hydroxy-dec-5-enoic acid 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:

2-deoxy-D-ribose (22900-10-3,35536-75-5,36792-85-5,113890-34-9,113890-37-2,133813-23-7) → (Z)-(8S,9R)-8,10-Bis-(tert-butyl-diphenyl-silanyloxy)-9-hydroxy-dec-5-enoic acid (148903-92-8)

Guidance literature:

Multi-step reaction with 4 steps

1: HCl / diethyl ether / 0.25 h

2: pyridine / 0.5 h / Ambient temperature

3: 98 percent / BCl₃*Me₂S / diethyl ether / 0.17 h / Ambient temperature

4: 1.) NaN(TMS)2 / 1.) toluene, THF, from 0 deg C to -70 deg C, 2.) toluene, THF, from -70 deg C to 0 deg C

With pyridine; hydrogenchloride; boron trichloride - methyl sulfide complex; sodium hexamethyldisilazane; In diethyl ether;

DOI:10.1021/ja00066a056

Reference yield:

tert-butyl(((2R,3S)-3-((tert-butyldiphenylsilyl)oxy)-5-methoxytetrahydrofuran-2-yl)methoxy)diphenylsilane (148903-86-0) → (Z)-(8S,9R)-8,10-Bis-(tert-butyl-diphenyl-silanyloxy)-9-hydroxy-dec-5-enoic acid (148903-92-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / BCl₃*Me₂S / diethyl ether / 0.17 h / Ambient temperature

2: 1.) NaN(TMS)2 / 1.) toluene, THF, from 0 deg C to -70 deg C, 2.) toluene, THF, from -70 deg C to 0 deg C

With boron trichloride - methyl sulfide complex; sodium hexamethyldisilazane; In diethyl ether;

DOI:10.1021/ja00066a056

Reference yield:

1-O-methyl-2-deoxy-D-ribofuranoside (51255-17-5,51255-18-6,60134-26-1,89577-26-4,96038-80-1,96039-31-5,144301-84-8,144301-85-9) → (Z)-(8S,9R)-8,10-Bis-(tert-butyl-diphenyl-silanyloxy)-9-hydroxy-dec-5-enoic acid (148903-92-8)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 0.5 h / Ambient temperature

2: 98 percent / BCl₃*Me₂S / diethyl ether / 0.17 h / Ambient temperature

3: 1.) NaN(TMS)2 / 1.) toluene, THF, from 0 deg C to -70 deg C, 2.) toluene, THF, from -70 deg C to 0 deg C

With pyridine; boron trichloride - methyl sulfide complex; sodium hexamethyldisilazane; In diethyl ether;

DOI:10.1021/ja00066a056

upstream raw materials:

(4-carboxybutyl)triphenylphosphonium bromide

2-deoxy-D-ribose

tert-butyl(((2R,3S)-3-((tert-butyldiphenylsilyl)oxy)-5-methoxytetrahydrofuran-2-yl)methoxy)diphenylsilane

1-O-methyl-2-deoxy-D-ribofuranoside

Downstream raw materials:

(Z)-(9S,10R)-9-(tert-Butyl-diphenyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxymethyl)-3,4,5,8,9,10-hexahydro-oxecin-2-one

(Z)-(9S,10R)-9-(tert-Butyl-diphenyl-silanyloxy)-10-((1E,3Z)-4-iodo-buta-1,3-dienyl)-3,4,5,8,9,10-hexahydro-oxecin-2-one

(E)-3-[(Z)-(2R,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-10-oxo-3,4,7,8,9,10-hexahydro-2H-oxecin-2-yl]-propenal

(Z)-(9S,10R)-9-(tert-Butyl-diphenyl-silanyloxy)-10-hydroxymethyl-3,4,5,8,9,10-hexahydro-oxecin-2-one