(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

Base Information

• Chemical Name: (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
• CAS No.: 405115-98-2
• Molecular Formula: C₃₁H₄₂O₈Si
• Molecular Weight: 570.755

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 11 articles about (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 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: 73.0%

(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 (405115-97-1) → (R)-4-Acetoxy-5-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-2-phenyl-tetrahydro-furan-3-carboxylic 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 (405115-98-2)

Guidance literature:

With dirhodium tetraacetate; In dichloromethane; at 25 ℃; for 2h;

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) → (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 (405115-98-2)

Guidance literature:

Multi-step reaction with 11 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

10.1: 85 percent / pyridine / 1 h / 25 °C

11.1: 73 percent / Rh₂(OAc)4 / CH₂Cl₂ / 2 h / 25 °C

With pyridine; 2,6-dimethylpyridine; lead(IV) acetate; dirhodium tetraacetate; 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) → (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 (405115-98-2)

Guidance literature:

Multi-step reaction with 10 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

9.1: 85 percent / pyridine / 1 h / 25 °C

10.1: 73 percent / Rh₂(OAc)4 / CH₂Cl₂ / 2 h / 25 °C

With pyridine; 2,6-dimethylpyridine; lead(IV) acetate; dirhodium tetraacetate; 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:

(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

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

3-O-benzyl-D-glucopyranose

(S)-Benzyloxy-((2R,4R,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)-acetaldehyde

Downstream raw materials:

(R)-4-Benzyloxy-2-diazo-4-((2R,4R,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)-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

(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

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