(4R,5R,6R)-{6-[(1R,2S)-3-benzyloxy-2-methoxy-1-methyl-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-5,6-dihydro-4H-pyran-2-yl}-acetic acid methyl ester

Base Information

Chemical Name:(4R,5R,6R)-{6-[(1R,2S)-3-benzyloxy-2-methoxy-1-methyl-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-5,6-dihydro-4H-pyran-2-yl}-acetic acid methyl ester
CAS No.:804551-94-8
Molecular Formula:C₂₇H₄₄O₆Si
Molecular Weight:492.728
Hs Code.:

(4R,5R,6R)-{6-[(1R,2S)-3-benzyloxy-2-methoxy-1-methyl-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-5,6-dihydro-4H-pyran-2-yl}-acetic acid methyl ester

Synonyms:(4R,5R,6R)-{6-[(1R,2S)-3-benzyloxy-2-methoxy-1-methyl-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-5,6-dihydro-4H-pyran-2-yl}-acetic acid methyl ester

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Chemical Property of (4R,5R,6R)-{6-[(1R,2S)-3-benzyloxy-2-methoxy-1-methyl-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-5,6-dihydro-4H-pyran-2-yl}-acetic acid methyl ester

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Technology Process of (4R,5R,6R)-{6-[(1R,2S)-3-benzyloxy-2-methoxy-1-methyl-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-5,6-dihydro-4H-pyran-2-yl}-acetic acid methyl ester

There total 13 articles about (4R,5R,6R)-{6-[(1R,2S)-3-benzyloxy-2-methoxy-1-methyl-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-5,6-dihydro-4H-pyran-2-yl}-acetic 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: 80.0%

: 67-56-1
methanol

: 804552-06-5
(4R,5R,6R)-1-{6-[(1R,2S)-3-benzyloxy-2-methoxy-1-methyl-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-5,6-dihydro-4H-pyran-2-yl}-2-diazo-ethanone

: 804551-94-8
(4R,5R,6R)-{6-[(1R,2S)-3-benzyloxy-2-methoxy-1-methyl-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-5,6-dihydro-4H-pyran-2-yl}-acetic acid methyl ester

Guidance literature:: With pyridine; silver benzoate; at 20 ℃; for 24h;
DOI:10.1021/ol0480325

Reference yield:

: 60656-87-3
benzyloxyacetoaldehyde

: 804551-94-8
(4R,5R,6R)-{6-[(1R,2S)-3-benzyloxy-2-methoxy-1-methyl-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-5,6-dihydro-4H-pyran-2-yl}-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: 87 percent / SnCl₄ / CH₂Cl₂ / 12 h / -78 °C

2.1: 2.8 g / SbCl₅ / CH₂Cl₂ / -78 - -50 °C

3.1: 95 percent / Proton Sponge(R); molecular sieves 4 Angstroem / CH₂Cl₂ / 6 h

4.1: O₃ / methanol; CH₂Cl₂ / -78 °C

4.2: Me₂S / methanol; CH₂Cl₂ / 12 h / -78 - 20 °C

5.1: 85 percent / TfOH / CH₂Cl₂ / 24 h / -70 °C

6.1: 80 percent / m-CPBA / CH₂Cl₂ / 12 h / 20 °C

7.1: K₂CO₃ / methanol / 2 h / 20 °C

7.2: 65 percent / molecular sieves 4 Angstroem; PDC / CH₂Cl₂ / 2 h / 20 °C

8.1: 93 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 1 h / -78 °C

9.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / -78 °C

10.1: LiOH / tetrahydrofuran; methanol; H₂O / 3 h / 20 °C

11.1: (ClCO)2 / CH₂Cl₂; dimethylformamide / 0.25 h / 20 °C

12.1: 1.3 g / diethyl ether / 0.5 h / 0 °C

13.1: 80 percent / silver benzoate; pyridine / 24 h / 20 °C

With pyridine; 2,6-dimethylpyridine; lithium hydroxide; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; trifluorormethanesulfonic acid; 4 A molecular sieve; antimonypentachloride; silver benzoate; tin(IV) chloride; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; potassium carbonate; ozone; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 13.1: Arndt-Eistert reaction;
DOI:10.1021/ol0480325

Reference yield:

: 804551-90-4
(2R,3S)-4-benzyloxy-3-methoxy-2-methyl-butyraldehyde

: 804551-94-8
(4R,5R,6R)-{6-[(1R,2S)-3-benzyloxy-2-methoxy-1-methyl-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-5,6-dihydro-4H-pyran-2-yl}-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 85 percent / TfOH / CH₂Cl₂ / 24 h / -70 °C

2.1: 80 percent / m-CPBA / CH₂Cl₂ / 12 h / 20 °C

3.1: K₂CO₃ / methanol / 2 h / 20 °C

3.2: 65 percent / molecular sieves 4 Angstroem; PDC / CH₂Cl₂ / 2 h / 20 °C

4.1: 93 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 1 h / -78 °C

5.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / -78 °C

6.1: LiOH / tetrahydrofuran; methanol; H₂O / 3 h / 20 °C

7.1: (ClCO)2 / CH₂Cl₂; dimethylformamide / 0.25 h / 20 °C

8.1: 1.3 g / diethyl ether / 0.5 h / 0 °C

9.1: 80 percent / silver benzoate; pyridine / 24 h / 20 °C

With pyridine; 2,6-dimethylpyridine; lithium hydroxide; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; trifluorormethanesulfonic acid; silver benzoate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 9.1: Arndt-Eistert reaction;
DOI:10.1021/ol0480325