(3S,5S,7S)-7,9-Bis-benzyloxy-3,5-dihydroxy-2,2-dimethyl-nonanoic acid methyl ester

Base Information

Chemical Name:(3S,5S,7S)-7,9-Bis-benzyloxy-3,5-dihydroxy-2,2-dimethyl-nonanoic acid methyl ester
CAS No.:362623-99-2
Molecular Formula:C₂₆H₃₆O₆
Molecular Weight:444.568
Hs Code.:

Synonyms:(3S,5S,7S)-7,9-Bis-benzyloxy-3,5-dihydroxy-2,2-dimethyl-nonanoic acid methyl ester

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Chemical Property of (3S,5S,7S)-7,9-Bis-benzyloxy-3,5-dihydroxy-2,2-dimethyl-nonanoic acid methyl ester

Chemical Property:

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Technology Process of (3S,5S,7S)-7,9-Bis-benzyloxy-3,5-dihydroxy-2,2-dimethyl-nonanoic acid methyl ester

There total 14 articles about (3S,5S,7S)-7,9-Bis-benzyloxy-3,5-dihydroxy-2,2-dimethyl-nonanoic acid methyl ester 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:

: 100-39-0
benzyl bromide

: 362623-99-2
(3S,5S,7S)-7,9-Bis-benzyloxy-3,5-dihydroxy-2,2-dimethyl-nonanoic acid methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: 92 percent / NaH / tetrahydrofuran / 20 °C

2.1: 82 percent / PTSA / methanol / 20 °C

3.1: 91 percent / LiAlH₄ / tetrahydrofuran / Heating

4.1: 90 percent / D(-)DIPT; TBHP / Ti(O-i-Pr)4 / CH₂Cl₂ / 7 h / -20 °C

5.1: 90 percent / TPP; I₂; imidazole / diethyl ether; acetonitrile / 20 °C

6.1: 84 percent / Zn; NaI / methanol / Heating

7.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

8.1: BH₃*THF / tetrahydrofuran / 0 °C

8.2: 75 percent / H₂O₂; NaOH

9.1: 70 percent / (COCl)2; Et₃N; DMSO / CH₂Cl₂ / -78 - 0 °C

10.1: LDA / tetrahydrofuran / -78 - 0 °C

11.1: 82 percent / TBAF; HOAc / tetrahydrofuran / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; tert.-butylhydroperoxide; lithium aluminium tetrahydride; borane-THF; oxalyl dichloride; tetrabutyl ammonium fluoride; iodine; thiamine diphosphate; sodium hydride; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; sodium iodide; zinc; lithium diisopropyl amide; titanium(IV) isopropylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; 4.1: Sharpless asymmetric epoxidation;
DOI:10.1016/S0040-4039(01)00841-3

Reference yield:

: 94426-72-9
2-(2-(benzyloxy)ethyl)oxirane

: 362623-99-2
(3S,5S,7S)-7,9-Bis-benzyloxy-3,5-dihydroxy-2,2-dimethyl-nonanoic acid methyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: 43 percent / Jacobsen's catalyst (Co-salen) / H₂O / 12 h / 0 - 20 °C

2.1: 90 percent / n-BuLi; BF₃*Et₂O / tetrahydrofuran / -78 °C

3.1: 92 percent / NaH / tetrahydrofuran / 20 °C

4.1: 82 percent / PTSA / methanol / 20 °C

5.1: 91 percent / LiAlH₄ / tetrahydrofuran / Heating

6.1: 90 percent / D(-)DIPT; TBHP / Ti(O-i-Pr)4 / CH₂Cl₂ / 7 h / -20 °C

7.1: 90 percent / TPP; I₂; imidazole / diethyl ether; acetonitrile / 20 °C

8.1: 84 percent / Zn; NaI / methanol / Heating

9.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

10.1: BH₃*THF / tetrahydrofuran / 0 °C

10.2: 75 percent / H₂O₂; NaOH

11.1: 70 percent / (COCl)2; Et₃N; DMSO / CH₂Cl₂ / -78 - 0 °C

12.1: LDA / tetrahydrofuran / -78 - 0 °C

13.1: 82 percent / TBAF; HOAc / tetrahydrofuran / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; tert.-butylhydroperoxide; lithium aluminium tetrahydride; n-butyllithium; borane-THF; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; iodine; thiamine diphosphate; sodium hydride; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; sodium iodide; zinc; lithium diisopropyl amide; titanium(IV) isopropylate; (R,R)-(-)-N,N’-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II); In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetonitrile; 6.1: Sharpless asymmetric epoxidation;
DOI:10.1016/S0040-4039(01)00841-3

Reference yield:

: 85960-55-0
(S)-(2-phenylmethoxyethyl)oxirane

: 362623-99-2
(3S,5S,7S)-7,9-Bis-benzyloxy-3,5-dihydroxy-2,2-dimethyl-nonanoic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: 90 percent / n-BuLi; BF₃*Et₂O / tetrahydrofuran / -78 °C

2.1: 92 percent / NaH / tetrahydrofuran / 20 °C

3.1: 82 percent / PTSA / methanol / 20 °C

4.1: 91 percent / LiAlH₄ / tetrahydrofuran / Heating

5.1: 90 percent / D(-)DIPT; TBHP / Ti(O-i-Pr)4 / CH₂Cl₂ / 7 h / -20 °C

6.1: 90 percent / TPP; I₂; imidazole / diethyl ether; acetonitrile / 20 °C

7.1: 84 percent / Zn; NaI / methanol / Heating

8.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

9.1: BH₃*THF / tetrahydrofuran / 0 °C

9.2: 75 percent / H₂O₂; NaOH

10.1: 70 percent / (COCl)2; Et₃N; DMSO / CH₂Cl₂ / -78 - 0 °C

11.1: LDA / tetrahydrofuran / -78 - 0 °C

12.1: 82 percent / TBAF; HOAc / tetrahydrofuran / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; tert.-butylhydroperoxide; lithium aluminium tetrahydride; n-butyllithium; borane-THF; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; iodine; thiamine diphosphate; sodium hydride; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; sodium iodide; zinc; lithium diisopropyl amide; titanium(IV) isopropylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; 5.1: Sharpless asymmetric epoxidation;
DOI:10.1016/S0040-4039(01)00841-3