(3R,4S)-4-tert-butyloxycarbonylamino-1,2-dihydroxy-3-tetrahydropyranyloxy-5-3'-(N-mesitylene-2-sulfonyl)indolylpentane

Base Information

• Chemical Name: (3R,4S)-4-tert-butyloxycarbonylamino-1,2-dihydroxy-3-tetrahydropyranyloxy-5-3'-(N-mesitylene-2-sulfonyl)indolylpentane
• CAS No.: 195325-59-8
• Molecular Formula: C₃₂H₄₄N₂O₈S
• Molecular Weight: 616.776
• Mol file: 195325-59-8.mol

Synonyms:(3R,4S)-4-tert-butyloxycarbonylamino-1,2-dihydroxy-3-tetrahydropyranyloxy-5-3'-(N-mesitylene-2-sulfonyl)indolylpentane

Chemical Property of (3R,4S)-4-tert-butyloxycarbonylamino-1,2-dihydroxy-3-tetrahydropyranyloxy-5-3'-(N-mesitylene-2-sulfonyl)indolylpentane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-4-tert-butyloxycarbonylamino-1,2-dihydroxy-3-tetrahydropyranyloxy-5-3'-(N-mesitylene-2-sulfonyl)indolylpentane

There total 4 articles about (3R,4S)-4-tert-butyloxycarbonylamino-1,2-dihydroxy-3-tetrahydropyranyloxy-5-3'-(N-mesitylene-2-sulfonyl)indolylpentane 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: 83.0%

(3S,4S)-4-tert-butyloxycarbonylamino-3-tetrahydropyranyloxy-5-3'-(N-mesitylene-2-sulfonyl)indolyl-1-pentene (195325-57-6) → (3R,4S)-4-tert-butyloxycarbonylamino-1,2-dihydroxy-3-tetrahydropyranyloxy-5-3'-(N-mesitylene-2-sulfonyl)indolylpentane (195325-59-8)

Guidance literature:

With tert.-butylhydroperoxide; osmium(VIII) oxide; tetraethylammonium chloride; sodium acetate; In acetone; tert-butyl alcohol; for 96h; Ambient temperature;

DOI:10.1248/cpb.45.1259

Reference yield:

{(S)-1-Formyl-2-[1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indol-3-yl]-ethyl}-carbamic acid tert-butyl ester (1026493-36-6) → (3R,4S)-4-tert-butyloxycarbonylamino-1,2-dihydroxy-3-tetrahydropyranyloxy-5-3'-(N-mesitylene-2-sulfonyl)indolylpentane (195325-59-8)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / 20 h / 0 °C

2: 84 percent / p-toluenesulfonic acid / CH₂Cl₂ / 16 h / Ambient temperature

3: 83 percent / tetraethylammonium chloride, AcONa, 70percent aq. tert-butylhydroxyperoxide, OsO₄ / acetone; 2-methyl-propan-2-ol / 96 h / Ambient temperature

With tert.-butylhydroperoxide; osmium(VIII) oxide; tetraethylammonium chloride; sodium acetate; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; acetone; tert-butyl alcohol;

DOI:10.1248/cpb.45.1259

Reference yield:

{(S)-1-(Methoxy-methyl-carbamoyl)-2-[1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indol-3-yl]-ethyl}-carbamic acid tert-butyl ester (195325-55-4) → (3R,4S)-4-tert-butyloxycarbonylamino-1,2-dihydroxy-3-tetrahydropyranyloxy-5-3'-(N-mesitylene-2-sulfonyl)indolylpentane (195325-59-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1 M DIBAL / toluene; tetrahydrofuran / 1.5 h / -78 °C

2: tetrahydrofuran / 20 h / 0 °C

3: 84 percent / p-toluenesulfonic acid / CH₂Cl₂ / 16 h / Ambient temperature

4: 83 percent / tetraethylammonium chloride, AcONa, 70percent aq. tert-butylhydroxyperoxide, OsO₄ / acetone; 2-methyl-propan-2-ol / 96 h / Ambient temperature

With tert.-butylhydroperoxide; osmium(VIII) oxide; tetraethylammonium chloride; sodium acetate; diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; acetone; toluene; tert-butyl alcohol;

DOI:10.1248/cpb.45.1259

upstream raw materials:

(3S,4S)-4-tert-butyloxycarbonylamino-3-tetrahydropyranyloxy-5-3'-(N-mesitylene-2-sulfonyl)indolyl-1-pentene

{(S)-1-Formyl-2-[1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indol-3-yl]-ethyl}-carbamic acid tert-butyl ester

{(S)-1-(Methoxy-methyl-carbamoyl)-2-[1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indol-3-yl]-ethyl}-carbamic acid tert-butyl ester

(3S,4S)-4-tert-butyloxycarbonylamino-3-hydroxy-5-3'-(N-mesitylene-2-sulfonyl)indolyl-1-pentene

Downstream raw materials:

{(1S,2R)-3-Oxo-2-(tetrahydro-pyran-2-yloxy)-1-[1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indol-3-ylmethyl]-propyl}-carbamic acid tert-butyl ester