(S)-3-[(2S,3R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-3-nitro-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-tert-butoxycarbonylamino-propionic acid tert-butyl ester

Base Information

• Chemical Name: (S)-3-[(2S,3R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-3-nitro-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-tert-butoxycarbonylamino-propionic acid tert-butyl ester
• CAS No.: 365455-41-0
• Molecular Formula: C₆₆H₇₈N₂O₁₆
• Molecular Weight: 1155.35

Synonyms:(S)-3-[(2S,3R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-3-nitro-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-tert-butoxycarbonylamino-propionic acid tert-butyl ester

Chemical Property of (S)-3-[(2S,3R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-3-nitro-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-tert-butoxycarbonylamino-propionic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-[(2S,3R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-3-nitro-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-tert-butoxycarbonylamino-propionic acid tert-butyl ester

There total 3 articles about (S)-3-[(2S,3R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-3-nitro-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-tert-butoxycarbonylamino-propionic acid tert-butyl 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: 91.0%

N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester (71630-31-4,7738-22-9) + (2R,3R,4R)-3-Benzyloxy-2-benzyloxymethyl-5-nitro-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran (365455-39-6) → (S)-3-[(2S,3R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-3-nitro-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-tert-butoxycarbonylamino-propionic acid tert-butyl ester (365455-41-0)

Guidance literature:

With potassium tert-butylate; In toluene;

DOI:10.1002/1521-3773(20010716)40:14<2654::AID-ANIE2654>3.0.CO;2-L

Reference yield:

benzyl bromide (100-39-0) → (S)-3-[(2S,3R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-3-nitro-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-tert-butoxycarbonylamino-propionic acid tert-butyl ester (365455-41-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / dimethylformamide

2.1: Ac₂O; conc. HNO₃ / -50 - -22 °C

2.2: 88 percent / Et₃N / CH₂Cl₂

3.1: 91 percent / KOBu-t / toluene

With potassium tert-butylate; nitric acid; acetic anhydride; sodium hydride; In N,N-dimethyl-formamide; toluene;

DOI:10.1002/1521-3773(20010716)40:14<2654::AID-ANIE2654>3.0.CO;2-L

Reference yield:

(2R,3R,4R)-3-Benzyloxy-2-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran (366799-53-3) → (S)-3-[(2S,3R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-3-nitro-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-tert-butoxycarbonylamino-propionic acid tert-butyl ester (365455-41-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Ac₂O; conc. HNO₃ / -50 - -22 °C

1.2: 88 percent / Et₃N / CH₂Cl₂

2.1: 91 percent / KOBu-t / toluene

With potassium tert-butylate; nitric acid; acetic anhydride; In toluene;

DOI:10.1002/1521-3773(20010716)40:14<2654::AID-ANIE2654>3.0.CO;2-L

upstream raw materials:

N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester

(2R,3R,4R)-3-Benzyloxy-2-benzyloxymethyl-5-nitro-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran

benzyl bromide

(2R,3R,4R)-3-Benzyloxy-2-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran

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