(2S,6R)-6-[(S)-1-({(2S,6R)-6-[(S)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carbonyl}-amino)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carboxylic acid ethyl ester

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Chemical Name:(2S,6R)-6-[(S)-1-({(2S,6R)-6-[(S)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carbonyl}-amino)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carboxylic acid ethyl ester
CAS No.:444687-41-6
Molecular Formula:C₃₈H₆₆N₂O₉Si₂
Molecular Weight:751.121
Hs Code.:

(2S,6R)-6-[(S)-1-({(2S,6R)-6-[(S)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carbonyl}-amino)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carboxylic acid ethyl ester

Synonyms:(2S,6R)-6-[(S)-1-({(2S,6R)-6-[(S)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carbonyl}-amino)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carboxylic acid ethyl ester

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Chemical Property of (2S,6R)-6-[(S)-1-({(2S,6R)-6-[(S)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carbonyl}-amino)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carboxylic acid ethyl ester

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Technology Process of (2S,6R)-6-[(S)-1-({(2S,6R)-6-[(S)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carbonyl}-amino)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carboxylic acid ethyl ester

There total 9 articles about (2S,6R)-6-[(S)-1-({(2S,6R)-6-[(S)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carbonyl}-amino)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carboxylic acid ethyl 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: 81.0%

: 444687-39-2
(2S,6R)-6-[(S)-1-Amino-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carboxylic acid ethyl ester

: 444687-37-0
(2S,6R)-6-[(S)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carboxylic acid

: 444687-41-6
(2S,6R)-6-[(S)-1-({(2S,6R)-6-[(S)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carbonyl}-amino)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carboxylic acid ethyl ester

Guidance literature:: With benzotriazol-1-ol; diisopropyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 24h;
DOI:10.1021/ol0261480

Reference yield:

: 98894-85-0
(Z)-6-chlorohex-2-en-1-ol tert-butyldimethylsilyl ether

: 444687-41-6
(2S,6R)-6-[(S)-1-({(2S,6R)-6-[(S)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carbonyl}-amino)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: magnesium; Br(CH₂)2Br / tetrahydrofuran / 3 h / Heating

1.2: 94 percent / tetrahydrofuran / 3 h / -78 - 20 °C

2.1: 85 percent / oxalyl chloride; DMSO; NEt₃ / CH₂Cl₂ / 6.5 h / -78 - 20 °C

3.1: 94 percent / Zn(BH₄)2; CeCl₃*7H₂O / diethyl ether; methanol / 4 h / 0 °C

4.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

5.1: 8.27 g / 2,6-lutidine / CH₂Cl₂ / 1 h / -15 °C

6.1: 96 percent / Pd₂(dba)3*CHCl₃; (S,S)-1,2-di[2'-(diphenylphosphino)benzamido]cyclohexane / tetrahydrofuran; diethyl ether / 12 h / 20 °C

7.1: ozone / CH₂Cl₂ / -78 °C

7.2: triphenylphosphine / CH₂Cl₂ / 4 h / cooling

8.1: 5.47 g / sodium hypochlorite; NaH₂PO₄*H₂O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 2 h / 20 °C

9.1: 83 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 18 h / 20 °C

10.1: 98 percent / camphorsulfonic acid / methanol; tetrahydrofuran / 12 h / 50 °C

11.1: 90 percent / imidazole / CH₂Cl₂ / 1 h / 20 °C

12.1: 100 percent / hydrogen / Pd/C / ethyl acetate; methanol / 12 h

13.1: 81 percent / diisopropylcarbodiimide; 1-hydroxybenzotriazole / CH₂Cl₂; dimethylformamide / 24 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl); tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium hypochlorite; sodium dihydrogenphosphate; cerium(III) chloride; zinc(II) tetrahydroborate; 2-methyl-but-2-ene; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; benzotriazol-1-ol; ozone; magnesium; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; ethylene dibromide; triethylamine; diisopropyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 1.2: Grignard addition / 2.1: Swern oxidation / 3.1: Luche reduction;
DOI:10.1021/ol0261480

Reference yield:

: 444687-29-0
(S)-2,2-Dimethyl-4-((2R,6S)-6-vinyl-tetrahydro-pyran-2-yl)-oxazolidine-3-carboxylic acid benzyl ester

: 444687-41-6
(2S,6R)-6-[(S)-1-({(2S,6R)-6-[(S)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carbonyl}-amino)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: ozone / CH₂Cl₂ / -78 °C

1.2: triphenylphosphine / CH₂Cl₂ / 4 h / cooling

2.1: 5.47 g / sodium hypochlorite; NaH₂PO₄*H₂O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 2 h / 20 °C

3.1: 83 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 18 h / 20 °C

4.1: 98 percent / camphorsulfonic acid / methanol; tetrahydrofuran / 12 h / 50 °C

5.1: 90 percent / imidazole / CH₂Cl₂ / 1 h / 20 °C

6.1: 100 percent / hydrogen / Pd/C / ethyl acetate; methanol / 12 h

7.1: 81 percent / diisopropylcarbodiimide; 1-hydroxybenzotriazole / CH₂Cl₂; dimethylformamide / 24 h / 20 °C

With 1H-imidazole; sodium hypochlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; camphor-10-sulfonic acid; hydrogen; benzotriazol-1-ol; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;
DOI:10.1021/ol0261480