Acetic acid (2S,3R,4S,6S)-3-benzyloxycarbonylamino-6-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-phenyl-ethoxy]-2-methyl-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,6S)-3-benzyloxycarbonylamino-6-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-phenyl-ethoxy]-2-methyl-tetrahydro-pyran-4-yl ester
• CAS No.: 201158-68-1
• Molecular Formula: C₄₀H₄₇NO₇Si
• Molecular Weight: 681.901
• Mol file: 201158-68-1.mol

Synonyms:Acetic acid (2S,3R,4S,6S)-3-benzyloxycarbonylamino-6-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-phenyl-ethoxy]-2-methyl-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2S,3R,4S,6S)-3-benzyloxycarbonylamino-6-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-phenyl-ethoxy]-2-methyl-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3R,4S,6S)-3-benzyloxycarbonylamino-6-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-phenyl-ethoxy]-2-methyl-tetrahydro-pyran-4-yl ester

There total 7 articles about Acetic acid (2S,3R,4S,6S)-3-benzyloxycarbonylamino-6-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-phenyl-ethoxy]-2-methyl-tetrahydro-pyran-4-yl 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:

(2R,3S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxybutanoic acid (5618-95-1,19728-63-3,41151-16-0,85995-53-5,119221-16-8,80384-27-6) → Acetic acid (2S,3R,4S,6S)-3-benzyloxycarbonylamino-6-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-phenyl-ethoxy]-2-methyl-tetrahydro-pyran-4-yl ester (201158-68-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 73 percent / p-toluenesulfonic acid / benzene / 3 h / Heating

2: 72 percent / cyanuric chloride, pyridine / CH₂Cl₂ / 50 h

3: 86 percent / tetrahydrofuran; diethyl ether / 2.5 h / -78 °C

4: 64 percent / TFA / methanol / 0.25 h

5: 78 percent / tetramethylammonium triacetoxyborohydride / acetic acid; acetonitrile / 4 h / -28 °C

6: 82 percent / ozone / methanol / 1 h / -78 °C

7: 1.) pyridine, 2.) BF₃-Et₂O / 2.) toluene, 0 deg C, 2 h

With pyridine; 1,3,5-trichloro-2,4,6-triazine; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; ozone; trifluoroacetic acid; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetic acid; acetonitrile; benzene;

DOI:10.1021/jo971380i

Reference yield:

[(1R,2S)-2-Hydroxy-1-((S)-1-hydroxy-ethyl)-pent-4-enyl]-carbamic acid benzyl ester (201158-42-1) → Acetic acid (2S,3R,4S,6S)-3-benzyloxycarbonylamino-6-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-phenyl-ethoxy]-2-methyl-tetrahydro-pyran-4-yl ester (201158-68-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / ozone / methanol / 1 h / -78 °C

2: 1.) pyridine, 2.) BF₃-Et₂O / 2.) toluene, 0 deg C, 2 h

With pyridine; boron trifluoride diethyl etherate; ozone; In methanol;

DOI:10.1021/jo971380i

Reference yield:

(2S,3R)-3-benzyloxycarbonylamino-2-hydroxyhept-6-en-4-one (201158-37-4) → Acetic acid (2S,3R,4S,6S)-3-benzyloxycarbonylamino-6-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-phenyl-ethoxy]-2-methyl-tetrahydro-pyran-4-yl ester (201158-68-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / tetramethylammonium triacetoxyborohydride / acetic acid; acetonitrile / 4 h / -28 °C

2: 82 percent / ozone / methanol / 1 h / -78 °C

3: 1.) pyridine, 2.) BF₃-Et₂O / 2.) toluene, 0 deg C, 2 h

With pyridine; boron trifluoride diethyl etherate; ozone; tetramethylammonium triacetoxyborohydride; In methanol; acetic acid; acetonitrile;

DOI:10.1021/jo971380i

upstream raw materials:

(R)-2-{[(tert-Butyl)diphenylsilyl]oxy}-1-phenylethanol

acetic acid

(2R,3S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxybutanoic acid

[(1R,2S)-2-Hydroxy-1-((S)-1-hydroxy-ethyl)-pent-4-enyl]-carbamic acid benzyl ester

Downstream raw materials:

(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionic acid (R)-2-((2S,4S,5S,6S)-5-benzyloxycarbonylamino-4-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-phenyl-ethyl ester

[(2S,3S,4S,6S)-4-Hydroxy-6-((R)-2-hydroxy-1-phenyl-ethoxy)-2-methyl-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

{(2S,3S,4S,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-phenyl-ethoxy]-4-hydroxy-2-methyl-tetrahydro-pyran-3-yl}-carbamic acid benzyl ester