(3R,4R,5S,7S)-8-Benzyloxy-3,4,5-tris-methoxymethoxy-7-methyl-octan-1-ol

Base Information

• Chemical Name: (3R,4R,5S,7S)-8-Benzyloxy-3,4,5-tris-methoxymethoxy-7-methyl-octan-1-ol
• CAS No.: 269076-57-5
• Molecular Formula: C₂₂H₃₈O₈
• Molecular Weight: 430.539
• Mol file: 269076-57-5.mol

Synonyms:(3R,4R,5S,7S)-8-Benzyloxy-3,4,5-tris-methoxymethoxy-7-methyl-octan-1-ol

Chemical Property of (3R,4R,5S,7S)-8-Benzyloxy-3,4,5-tris-methoxymethoxy-7-methyl-octan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5S,7S)-8-Benzyloxy-3,4,5-tris-methoxymethoxy-7-methyl-octan-1-ol

There total 14 articles about (3R,4R,5S,7S)-8-Benzyloxy-3,4,5-tris-methoxymethoxy-7-methyl-octan-1-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: 64.0%

((2S,4S,5R,6R)-4,5,6-Tris-methoxymethoxy-2-methyl-oct-7-enyloxymethyl)-benzene (269076-56-4) → (3R,4R,5S,7S)-8-Benzyloxy-3,4,5-tris-methoxymethoxy-7-methyl-octan-1-ol (269076-57-5)

Guidance literature:

((2S,4S,5R,6R)-4,5,6-Tris-methoxymethoxy-2-methyl-oct-7-enyloxymethyl)-benzene; With borane-THF; In tetrahydrofuran; at 0 ℃; for 10h;

With sodium hydroxide; dihydrogen peroxide; In methanol; water; at 0 - 23 ℃; for 2.5h;

DOI:10.1016/S0040-4039(00)00062-9

Reference yield:

(4aR,6S,7R,8S,8aR)-6-Methoxy-7,8-bis-methoxymethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine → (3R,4R,5S,7S)-8-Benzyloxy-3,4,5-tris-methoxymethoxy-7-methyl-octan-1-ol (269076-57-5)

Guidance literature:

Multi-step reaction with 14 steps

1.1: NBS; BaCO₃ / AIBN / CCl₄ / 1 h / reflux

2.1: Zn / ethanol; H₂O / 3 h / reflux

3.1: benzene / 23 h / 23 °C

4.1: NaBH₄; CuCl₂ / methanol / 3 h / 23 °C

5.1: NaOMe / methanol / 7 h / 23 °C

6.1: 88 percent / (i-Pr)2EtN / CH₂Cl₂ / 48 h / 23 °C

7.1: 92 percent / NaOH / methanol; H₂O / 18 h / 0 °C

8.1: 97 percent / PivCl; Et₃N; LiCl / tetrahydrofuran / 6.5 h / -20 - 23 °C

9.1: 77 percent / LDA / tetrahydrofuran / 22 h / -78 - -40 °C

10.1: LAH / tetrahydrofuran / 0.58 h / 0 °C

11.1: 92 percent / t-BuOK / tetrahydrofuran / 5.5 h / 0 °C

12.1: 78 percent / 4 percent HCl-MeOH / 72 h / 23 °C

13.1: 100 percent / (i-Pr)2EtN / 48 h / 23 °C

14.1: BH₃-THF / tetrahydrofuran / 10 h / 0 °C

14.2: 64 percent / H₂O₂; NaOH / methanol; H₂O / 2.5 h / 0 - 23 °C

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; borane-THF; potassium tert-butylate; sodium methylate; pivaloyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; barium carbonate; lithium chloride; copper dichloride; zinc; lithium diisopropyl amide; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; methanol; tetrachloromethane; ethanol; dichloromethane; water; benzene; 1.1: Bromination / 2.1: Ring cleavage / 3.1: Condensation / 4.1: Reduction / 5.1: Hydrolysis / 6.1: Alkylation / 7.1: Hydrolysis / 8.1: Acylation / 9.1: Methylation / 10.1: Reduction / 11.1: Alkylation / 12.1: Hydrolysis / 13.1: Etherification / 14.1: Addition / 14.2: Oxidation;

DOI:10.1016/S0040-4039(00)00062-9

Reference yield:

4-O-Benzoyl-2,3-di-O-methoxymethyl-5,6-didesoxy-D-xylo-hex-5-enose (73111-10-1) → (3R,4R,5S,7S)-8-Benzyloxy-3,4,5-tris-methoxymethoxy-7-methyl-octan-1-ol (269076-57-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: benzene / 23 h / 23 °C

2.1: NaBH₄; CuCl₂ / methanol / 3 h / 23 °C

3.1: NaOMe / methanol / 7 h / 23 °C

4.1: 88 percent / (i-Pr)2EtN / CH₂Cl₂ / 48 h / 23 °C

5.1: 92 percent / NaOH / methanol; H₂O / 18 h / 0 °C

6.1: 97 percent / PivCl; Et₃N; LiCl / tetrahydrofuran / 6.5 h / -20 - 23 °C

7.1: 77 percent / LDA / tetrahydrofuran / 22 h / -78 - -40 °C

8.1: LAH / tetrahydrofuran / 0.58 h / 0 °C

9.1: 92 percent / t-BuOK / tetrahydrofuran / 5.5 h / 0 °C

10.1: 78 percent / 4 percent HCl-MeOH / 72 h / 23 °C

11.1: 100 percent / (i-Pr)2EtN / 48 h / 23 °C

12.1: BH₃-THF / tetrahydrofuran / 10 h / 0 °C

12.2: 64 percent / H₂O₂; NaOH / methanol; H₂O / 2.5 h / 0 - 23 °C

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; borane-THF; potassium tert-butylate; sodium methylate; pivaloyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; copper dichloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; benzene; 1.1: Condensation / 2.1: Reduction / 3.1: Hydrolysis / 4.1: Alkylation / 5.1: Hydrolysis / 6.1: Acylation / 7.1: Methylation / 8.1: Reduction / 9.1: Alkylation / 10.1: Hydrolysis / 11.1: Etherification / 12.1: Addition / 12.2: Oxidation;

DOI:10.1016/S0040-4039(00)00062-9

upstream raw materials:

((2S,4S,5R,6R)-4,5,6-Tris-methoxymethoxy-2-methyl-oct-7-enyloxymethyl)-benzene

4-O-Benzoyl-2,3-di-O-methoxymethyl-5,6-didesoxy-D-xylo-hex-5-enose

(4S,5S,6R)-6-Hydroxy-4,5-bis-methoxymethoxy-oct-7-enoic acid methyl ester

Benzoic acid (E)-(1R,2R,3S)-5-methoxycarbonyl-2,3-bis-methoxymethoxy-1-vinyl-pent-4-enyl ester

Downstream raw materials:

(3R,4R,5S,7S)-8-Benzyloxy-3,4,5-tris-methoxymethoxy-7-methyl-octanoic acid methoxymethyl ester

(3R,4R,5S,7S)-8-Benzyloxy-3,4,5-tris-methoxymethoxy-7-methyl-octanoic acid

(3R,4R,5S,7S)-8-Benzyloxy-3,4,5-tris-methoxymethoxy-7-methyl-octanal