(S)-2-(3,4-Dimethoxy-benzyloxy)-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-N-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-acetamide

Base Information

• Chemical Name: (S)-2-(3,4-Dimethoxy-benzyloxy)-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-N-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-acetamide
• CAS No.: 128271-11-4
• Molecular Formula: C₃₄H₄₉NO₁₃
• Molecular Weight: 679.762
• Mol file: 128271-11-4.mol

Synonyms:

Chemical Property of (S)-2-(3,4-Dimethoxy-benzyloxy)-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-N-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-(3,4-Dimethoxy-benzyloxy)-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-N-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-acetamide

There total 33 articles about (S)-2-(3,4-Dimethoxy-benzyloxy)-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-N-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-acetamide 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: 42.0%

(S)-2-(3,4-Dimethoxy-benzyloxy)-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-N-[(4R,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-acetamide (128271-11-4,128385-71-7) → (S)-2-(3,4-Dimethoxy-benzyloxy)-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-N-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-acetamide (128271-11-4,128385-71-7)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; Heating;

DOI:10.1021/jo00301a007

Reference yield:

((2S,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-3,3-dimethyl-tetrahydro-pyran-2-yl)-methanol (128271-01-2) → (S)-2-(3,4-Dimethoxy-benzyloxy)-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-N-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-acetamide (128271-11-4,128385-71-7)

Guidance literature:

Multi-step reaction with 11 steps

2: OsO₄ / N,N'-bis(2,4,6-trimethylbenzyl)-(S,S)-1,2-diphenyl-1,2-diaminoethane / CH₂Cl₂ / -90 °C

5: H₂ / Pd(OH)2 on C / ethyl acetate / Ambient temperature

6: hydrochlorid acid / 0 °C

7: Et₃N, DMAP / CH₂Cl₂ / -60 °C

8: (n-Bu₄N)N₃ / CH₂Cl₂ / -78 deg C to room temperature

9: H₂ / Pd on C / ethyl acetate / Ambient temperature

11: 42 percent / potassium tert-butoxide / tetrahydrofuran / Heating

With hydrogenchloride; dmap; osmium(VIII) oxide; 1,2-diphenyl-N,N'-bis[(2,4,6-trimethylphenyl)methyl]-1,2-diaminoethane; potassium tert-butylate; hydrogen; tetrabutylammoniun azide; triethylamine; palladium on activated charcoal; palladium hydroxide - carbon; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1021/jo00301a007

Reference yield:

(2R,4S,5R,6S)-2-Allyl-5-benzyloxy-4,6-dimethoxy-3,3-dimethyl-tetrahydro-pyran (128271-02-3) → (S)-2-(3,4-Dimethoxy-benzyloxy)-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-N-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-acetamide (128271-11-4,128385-71-7)

Guidance literature:

Multi-step reaction with 10 steps

1: OsO₄ / N,N'-bis(2,4,6-trimethylbenzyl)-(S,S)-1,2-diphenyl-1,2-diaminoethane / CH₂Cl₂ / -90 °C

4: H₂ / Pd(OH)2 on C / ethyl acetate / Ambient temperature

5: hydrochlorid acid / 0 °C

6: Et₃N, DMAP / CH₂Cl₂ / -60 °C

7: (n-Bu₄N)N₃ / CH₂Cl₂ / -78 deg C to room temperature

8: H₂ / Pd on C / ethyl acetate / Ambient temperature

10: 42 percent / potassium tert-butoxide / tetrahydrofuran / Heating

With hydrogenchloride; dmap; osmium(VIII) oxide; 1,2-diphenyl-N,N'-bis[(2,4,6-trimethylphenyl)methyl]-1,2-diaminoethane; potassium tert-butylate; hydrogen; tetrabutylammoniun azide; triethylamine; palladium on activated charcoal; palladium hydroxide - carbon; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1021/jo00301a007

upstream raw materials:

(S)-4-((4aS,6R,8S,8aR)-4-Amino-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl)-[1,3]dioxolan-2-one

(+)-methyl pederate

((2S,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-3,3-dimethyl-tetrahydro-pyran-2-yl)-methanol

(2R,4S,5R,6S)-2-Allyl-5-benzyloxy-4,6-dimethoxy-3,3-dimethyl-tetrahydro-pyran

Downstream raw materials:

(S)-2-(3,4-Dimethoxy-benzyloxy)-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-N-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-acetamide

mycalamide A