2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-bis-O-(1-methylethylidene)-D-erythro-pentose

Base Information

• Chemical Name: 2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-bis-O-(1-methylethylidene)-D-erythro-pentose
• CAS No.: 93292-42-3
• Molecular Formula: C₂₄H₃₂O₄Si
• Molecular Weight: 412.601
• Mol file: 93292-42-3.mol

Synonyms:2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-bis-O-(1-methylethylidene)-D-erythro-pentose

Chemical Property of 2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-bis-O-(1-methylethylidene)-D-erythro-pentose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-bis-O-(1-methylethylidene)-D-erythro-pentose

There total 11 articles about 2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-bis-O-(1-methylethylidene)-D-erythro-pentose 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: 84.0%

2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-O-isopropylidene-D-erythro-pentose diethyl dithioacetal (93292-41-2) → 2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-bis-O-(1-methylethylidene)-D-erythro-pentose (93292-42-3)

Guidance literature:

With periodic acid; In tetrahydrofuran; diethyl ether; 1.) 0 deg C, 3 min, 2.) room temp., 5 min;

DOI:10.1021/jo9813282

Reference yield:

1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,3-bis-ethylsulfanyl-propan-1-ol (67320-20-1,83692-41-5,94292-91-8,64722-95-8) → 2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-bis-O-(1-methylethylidene)-D-erythro-pentose (93292-42-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaHMDS / 1.) THF, -78 deg C, 0.5 h, 2.) THF, from -78 to 15 deg C, 22 h

2: 76 percent / N-chlorosuccinimide, aq. AgNO₃ / acetonitrile / 0.17 h / -20 °C

With N-chloro-succinimide; sodium hexamethyldisilazane; silver nitrate; In acetonitrile;

DOI:10.1021/ja00128a008

Reference yield:

2-deoxy-4,5-O-isopropylidene-D-erythro-pent-1-enose diethyl dithioacetal (64722-92-5) → 2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-bis-O-(1-methylethylidene)-D-erythro-pentose (93292-42-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / LiAlH₄ / tetrahydrofuran / 3.5 h / Ambient temperature

2: 1.) NaHMDS / 1.) THF, -78 deg C, 0.5 h, 2.) THF, from -78 to 15 deg C, 22 h

3: 76 percent / N-chlorosuccinimide, aq. AgNO₃ / acetonitrile / 0.17 h / -20 °C

With N-chloro-succinimide; lithium aluminium tetrahydride; sodium hexamethyldisilazane; silver nitrate; In tetrahydrofuran; acetonitrile;

DOI:10.1021/ja00128a008

upstream raw materials:

tert-Butyl-[(S)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,3-bis-ethylsulfanyl-propoxy]-diphenyl-silane

(S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3,3-bis-ethylsulfanyl-propan-1-ol

2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-O-isopropylidene-D-erythro-pentose diethyl dithioacetal

(2R,3S)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-hexene-1,2,3-triol

Downstream raw materials:

(2S,4Z)-2-(tert-butyldiphenylsilyloxy)hept-4-enal

(E)-(S)-5-(tert-Butyl-diphenyl-silanyloxy)-8-oxo-oct-6-enoic acid methyl ester

methyl 5(S)-(tert-butyldiphenylsilyl)oxy-6-oxo-hexanoate

C₃₅H₄₈O₅Si

Refernces

• 1、 Patel, Pranav,Gore, Vivek,Powell, William S.,Rokach, Joshua. "C20-trifluoro-5-oxo-ETE: A metabolically stable 5-oxo-ETE derivative". scheme or table. p. 1987 - 1990. Retrieved 2011/05/02.
• 2、 Shi, Xiao-Xin,Khanapure, Subhash P.,Rokach, Joshua. "Deblocking of dithioacetals and oxathioacetals using periodic acid under mild nonaqueous conditions". . p. 4331 - 4334. Retrieved 2007/10/03.