(S)-2-Hydroxy-N-methoxy-N-methyl-2-[(3R,4S,5R)-2,2,4-trimethyl-3-((R)-1-methyl-2-trityloxy-ethyl)-[1,2]oxasilolan-5-yl]-acetamide

Base Information

• Chemical Name: (S)-2-Hydroxy-N-methoxy-N-methyl-2-[(3R,4S,5R)-2,2,4-trimethyl-3-((R)-1-methyl-2-trityloxy-ethyl)-[1,2]oxasilolan-5-yl]-acetamide
• CAS No.: 139460-76-7
• Molecular Formula: C₃₂H₄₁NO₅Si
• Molecular Weight: 547.767
• Mol file: 139460-76-7.mol

Synonyms:

Chemical Property of (S)-2-Hydroxy-N-methoxy-N-methyl-2-[(3R,4S,5R)-2,2,4-trimethyl-3-((R)-1-methyl-2-trityloxy-ethyl)-[1,2]oxasilolan-5-yl]-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Hydroxy-N-methoxy-N-methyl-2-[(3R,4S,5R)-2,2,4-trimethyl-3-((R)-1-methyl-2-trityloxy-ethyl)-[1,2]oxasilolan-5-yl]-acetamide

There total 5 articles about (S)-2-Hydroxy-N-methoxy-N-methyl-2-[(3R,4S,5R)-2,2,4-trimethyl-3-((R)-1-methyl-2-trityloxy-ethyl)-[1,2]oxasilolan-5-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:

(3S,4R)-3-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2,4-trimethyl-[1,2]oxasilolane (103668-54-8,103729-89-1) → (S)-2-Hydroxy-N-methoxy-N-methyl-2-[(3R,4S,5R)-2,2,4-trimethyl-3-((R)-1-methyl-2-trityloxy-ethyl)-[1,2]oxasilolan-5-yl]-acetamide (139460-76-7)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / Pd/C

2: Swern oxidation

3: 12 h / Horner-Emmons olefination

4: OsO₄, NMO / acetone; H₂O

5: acetonitrile

With osmium(VIII) oxide; N-methyl-2-indolinone; hydrogen; palladium on activated charcoal; In water; acetone; acetonitrile;

DOI:10.1021/jo00032a007

Reference yield:

(S)-2-((3S,4R)-2,2,4-Trimethyl-[1,2]oxasilolan-3-yl)-propan-1-ol (139427-68-2,139559-31-2) → (S)-2-Hydroxy-N-methoxy-N-methyl-2-[(3R,4S,5R)-2,2,4-trimethyl-3-((R)-1-methyl-2-trityloxy-ethyl)-[1,2]oxasilolan-5-yl]-acetamide (139460-76-7)

Guidance literature:

Multi-step reaction with 4 steps

1: Swern oxidation

2: 12 h / Horner-Emmons olefination

3: OsO₄, NMO / acetone; H₂O

4: acetonitrile

With osmium(VIII) oxide; N-methyl-2-indolinone; In water; acetone; acetonitrile;

DOI:10.1021/jo00032a007

Reference yield:

(S)-2-((3R,4R)-2,2,4-Trimethyl-[1,2]oxasilolan-3-yl)-propionaldehyde → (S)-2-Hydroxy-N-methoxy-N-methyl-2-[(3R,4S,5R)-2,2,4-trimethyl-3-((R)-1-methyl-2-trityloxy-ethyl)-[1,2]oxasilolan-5-yl]-acetamide (139460-76-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 12 h / Horner-Emmons olefination

2: OsO₄, NMO / acetone; H₂O

3: acetonitrile

With osmium(VIII) oxide; N-methyl-2-indolinone; In water; acetone; acetonitrile;

DOI:10.1021/jo00032a007

upstream raw materials:

N-tritylpyridinium tetrafluoroborate

(S)-2-Hydroxy-2-[(3R,4S,5R)-3-((R)-2-hydroxy-1-methyl-ethyl)-2,2,4-trimethyl-[1,2]oxasilolan-5-yl]-N-methoxy-N-methyl-acetamide

(S)-2-((3S,4R)-2,2,4-Trimethyl-[1,2]oxasilolan-3-yl)-propan-1-ol

(E)-(S)-4-((3S,4R)-2,2,4-Trimethyl-[1,2]oxasilolan-3-yl)-pent-2-enoic acid methoxy-methyl-amide

Downstream raw materials:

(3R,4R,6R,8S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-2,6,8-trimethyl-9-trityloxy-non-1-en-5-one

(4S,5R,6R,8S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-2,6,8-trimethyl-9-trityloxy-non-1-en-3-one

(3R,4S,5R,6R,8S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-2,6,8-trimethyl-9-trityloxy-non-1-en-5-ol

(2S,3R,4R,6S)-3-Hydroxy-2-methoxy-4,6-dimethyl-7-trityloxy-heptanoic acid methoxy-methyl-amide