(R)-4-Benzyloxy-4-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-2-diazo-3-hydroxy-butyric acid ethyl ester

Base Information

• Chemical Name: (R)-4-Benzyloxy-4-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-2-diazo-3-hydroxy-butyric acid ethyl ester
• CAS No.: 405115-96-0
• Molecular Formula: C₂₉H₄₀N₂O₇Si
• Molecular Weight: 556.731

Synonyms:(R)-4-Benzyloxy-4-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-2-diazo-3-hydroxy-butyric acid ethyl ester

Chemical Property of (R)-4-Benzyloxy-4-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-2-diazo-3-hydroxy-butyric acid ethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (R)-4-Benzyloxy-4-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-2-diazo-3-hydroxy-butyric acid ethyl ester

There total 9 articles about (R)-4-Benzyloxy-4-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-2-diazo-3-hydroxy-butyric 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: 83.5%

diazoacetic acid ethyl ester (623-73-4) + (S)-Benzyloxy-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-acetaldehyde (402474-66-2) → (R)-4-Benzyloxy-4-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-2-diazo-3-hydroxy-butyric acid ethyl ester (405115-96-0)

Guidance literature:

diazoacetic acid ethyl ester; With diethylzinc; In hexane; dichloromethane; at -78 - -50 ℃;

(S)-Benzyloxy-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-acetaldehyde; In hexane; dichloromethane; at -50 - 20 ℃;

DOI:10.1016/S0040-4020(01)01074-2

Reference yield:

3-O-benzyl-1,2:5,6-di-O-isopropylidene-D-glucofuranose (18685-18-2,22331-21-1,23885-38-3,40982-92-1,65451-98-1,101475-83-6,134275-38-0,145625-96-3) → (R)-4-Benzyloxy-4-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-2-diazo-3-hydroxy-butyric acid ethyl ester (405115-96-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 74 percent / 1N H₂SO₄ / dioxane / 70 °C

2.1: 85 percent / CSA / dimethylformamide / 8 h / 25 °C

3.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.5 h / 0 °C

4.1: 56 percent / NaBH₄ / methanol / 0.5 h / 0 °C

5.1: 76 percent / pyridine / 3 h / 0 - 20 °C

6.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

7.1: 4.5 g / MeONa / methanol / 0.5 h / 0 °C

8.1: 86 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

9.1: Et₂Zn / CH₂Cl₂; hexane / -78 - -50 °C

9.2: 83.5 percent / CH₂Cl₂; hexane / -50 - 20 °C

With pyridine; 2,6-dimethylpyridine; lead(IV) acetate; sodium tetrahydroborate; oxalyl dichloride; sulfuric acid; camphor-10-sulfonic acid; diethylzinc; sodium methylate; dimethyl sulfoxide; triethylamine; In 1,4-dioxane; methanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)01074-2

Reference yield:

3-O-benzyl-D-glucopyranose (65877-63-6,97590-76-6,99396-09-5,5531-09-9) → (R)-4-Benzyloxy-4-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-2-diazo-3-hydroxy-butyric acid ethyl ester (405115-96-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 85 percent / CSA / dimethylformamide / 8 h / 25 °C

2.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.5 h / 0 °C

3.1: 56 percent / NaBH₄ / methanol / 0.5 h / 0 °C

4.1: 76 percent / pyridine / 3 h / 0 - 20 °C

5.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

6.1: 4.5 g / MeONa / methanol / 0.5 h / 0 °C

7.1: 86 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

8.1: Et₂Zn / CH₂Cl₂; hexane / -78 - -50 °C

8.2: 83.5 percent / CH₂Cl₂; hexane / -50 - 20 °C

With pyridine; 2,6-dimethylpyridine; lead(IV) acetate; sodium tetrahydroborate; oxalyl dichloride; camphor-10-sulfonic acid; diethylzinc; sodium methylate; dimethyl sulfoxide; triethylamine; In methanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)01074-2

upstream raw materials:

diazoacetic acid ethyl ester

(S)-Benzyloxy-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-acetaldehyde

3-O-benzyl-1,2:5,6-di-O-isopropylidene-D-glucofuranose

3-O-benzyl-D-glucopyranose

Downstream raw materials:

(R)-3-Acetoxy-4-benzyloxy-4-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-2-diazo-butyric acid ethyl ester

(Z)-(R)-2-Acetoxy-4-benzyloxy-4-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-but-2-enoic acid ethyl ester

(R)-4-Benzyloxy-4-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-2-hydrazono-butyric acid ethyl ester

(R)-4-Benzyloxy-4-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-2-diazo-butyric acid ethyl ester

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