(R)-4-{2-[(1Ξ,3R)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-5,5-dimethyl-[1,3]dioxan-2-yl}-2-methyl-butyraldehyde

Base Information

• Chemical Name: (R)-4-{2-[(1Ξ,3R)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-5,5-dimethyl-[1,3]dioxan-2-yl}-2-methyl-butyraldehyde
• CAS No.: 72297-83-7
• Molecular Formula: C₃₃H₅₀O₄Si
• Molecular Weight: 538.843

Synonyms:(R)-4-{2-[(1Ξ,3R)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-5,5-dimethyl-[1,3]dioxan-2-yl}-2-methyl-butyraldehyde

Chemical Property of (R)-4-{2-[(1Ξ,3R)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-5,5-dimethyl-[1,3]dioxan-2-yl}-2-methyl-butyraldehyde

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (R)-4-{2-[(1Ξ,3R)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-5,5-dimethyl-[1,3]dioxan-2-yl}-2-methyl-butyraldehyde

There total 18 articles about (R)-4-{2-[(1Ξ,3R)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-5,5-dimethyl-[1,3]dioxan-2-yl}-2-methyl-butyraldehyde 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:

(2R,4R,5R)-2,4-Dimethyl-hept-6-ene-1,5-diol (74231-27-9) → (R)-4-{2-[(1R,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-5,5-dimethyl-[1,3]dioxan-2-yl}-2-methyl-butyraldehyde (72297-83-7)

Guidance literature:

Multi-step reaction with 10 steps

1: 1) Et₃N, DMAP / 1)CH₂Cl₂

2: 1)LDA / 1) THF, 2) HMPA

3: Claisen rearrangement

4: KOH

5: 1) OsO₄, 2) camphorsulfonic acid / 1) pyridine, 2) benzene

6: PCC, NaOAc / CH₂Cl₂

7: aluminum amalgam / tetrahydrofuran; aq. ethanol

8: diethyl ether

9: 1) HC(OCH₃)3, TsOH, 2) LiAlH₄ / 1) CH₂Cl₂

10: Collins reagent

With dmap; potassium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; aluminium amalgam; Collins oxidation agent; camphor-10-sulfonic acid; sodium acetate; toluene-4-sulfonic acid; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; trimethyl orthoformate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane;

DOI:10.1021/jo01305a044

Reference yield:

(3aR,4R,6aS)-4-Methyl-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one (74231-22-4) → (R)-4-{2-[(1R,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-5,5-dimethyl-[1,3]dioxan-2-yl}-2-methyl-butyraldehyde (72297-83-7)

Guidance literature:

Multi-step reaction with 15 steps

2: 81 percent / LDA / tetrahydrofuran

3: 84 percent / 10percent HCl / tetrahydrofuran

4: 1) o-NO₂C₆H₄SeCN, Bu₃P, 2) 50percent H₂O₂ / 1)THF

5: 94 percent / LiAlH₄

6: 1) Et₃N, DMAP / 1)CH₂Cl₂

7: 1)LDA / 1) THF, 2) HMPA

8: Claisen rearrangement

9: KOH

10: 1) OsO₄, 2) camphorsulfonic acid / 1) pyridine, 2) benzene

11: PCC, NaOAc / CH₂Cl₂

12: aluminum amalgam / tetrahydrofuran; aq. ethanol

13: diethyl ether

14: 1) HC(OCH₃)3, TsOH, 2) LiAlH₄ / 1) CH₂Cl₂

15: Collins reagent

With hydrogenchloride; dmap; potassium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; ortho-nitrophenyl selenocyanate; tributylphosphine; aluminium amalgam; Collins oxidation agent; camphor-10-sulfonic acid; dihydrogen peroxide; sodium acetate; toluene-4-sulfonic acid; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; trimethyl orthoformate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane;

DOI:10.1021/jo01305a044

Reference yield:

(3S,5S,6S)-3,5-Dimethyl-6-vinyl-tetrahydro-pyran-2-one (74231-26-8) → (R)-4-{2-[(1R,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-5,5-dimethyl-[1,3]dioxan-2-yl}-2-methyl-butyraldehyde (72297-83-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 94 percent / LiAlH₄

2: 1) Et₃N, DMAP / 1)CH₂Cl₂

3: 1)LDA / 1) THF, 2) HMPA

4: Claisen rearrangement

5: KOH

6: 1) OsO₄, 2) camphorsulfonic acid / 1) pyridine, 2) benzene

7: PCC, NaOAc / CH₂Cl₂

8: aluminum amalgam / tetrahydrofuran; aq. ethanol

9: diethyl ether

10: 1) HC(OCH₃)3, TsOH, 2) LiAlH₄ / 1) CH₂Cl₂

11: Collins reagent

With dmap; potassium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; aluminium amalgam; Collins oxidation agent; camphor-10-sulfonic acid; sodium acetate; toluene-4-sulfonic acid; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; trimethyl orthoformate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane;

DOI:10.1021/jo01305a044

upstream raw materials:

(2R,4R,5R)-2,4-Dimethyl-hept-6-ene-1,5-diol

(3aR,4R,6aS)-4-Methyl-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one

(3S,5S,6S)-3,5-Dimethyl-6-vinyl-tetrahydro-pyran-2-one

(3S,5S,6S)-6-(2-Hydroxy-ethyl)-3,5-dimethyl-tetrahydro-pyran-2-one

Downstream raw materials:

calcimycin

2-{(2R)-6-[(1Ξ,3R)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-3c-methyl-3,4-dihydro-2H-pyran-2r-ylmethyl}-5-(methyl-trifluoroacetyl-amino)-benzooxazole-4-carboxylic acid methyl ester

2-((2R,3R)-5-{2-[(1Ξ,3R)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-5,5-dimethyl-[1,3]dioxan-2-yl}-2-hydroxy-3-methyl-pentyl)-5-(methyl-trifluoroacetyl-amino)-benzooxazole-4-carboxylic acid methyl ester

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