2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-6-allyloxy-4-[(2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-2-yloxy]-3,5-dihydroxy-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-6-allyloxy-4-[(2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-2-yloxy]-3,5-dihydroxy-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 276241-34-0
• Molecular Formula: C₃₄H₄₆N₂O₁₈
• Molecular Weight: 770.742
• Mol file: 276241-34-0.mol

Synonyms:2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-6-allyloxy-4-[(2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-2-yloxy]-3,5-dihydroxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-6-allyloxy-4-[(2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-2-yloxy]-3,5-dihydroxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-6-allyloxy-4-[(2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-2-yloxy]-3,5-dihydroxy-tetrahydro-pyran-2-ylmethyl ester

There total 6 articles about 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-6-allyloxy-4-[(2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-2-yloxy]-3,5-dihydroxy-tetrahydro-pyran-2-ylmethyl 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: 82.0%

allyl 6-O-pivaloyl-α-D-galactopyranoside (93619-87-5) + Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester (276241-24-8) → 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-6-allyloxy-4-[(2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-2-yloxy]-3,5-dihydroxy-tetrahydro-pyran-2-ylmethyl ester (276241-34-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -60 ℃; for 0.5h;

DOI:10.1016/S0960-894X(00)00107-4

Reference yield:

D-galactosamine (90-76-6,90-77-7,530-23-4,579-32-8,579-33-9,643-68-5,2596-19-2,6490-68-2,6490-70-6,6490-72-8,6490-73-9,6490-74-0,14196-84-0,14196-86-2,14257-69-3,58381-21-8) → 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-6-allyloxy-4-[(2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-2-yloxy]-3,5-dihydroxy-tetrahydro-pyran-2-ylmethyl ester (276241-34-0)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / 0 °C

2: 95 percent / pyridine; DMAP

3: 87 percent / hydrazine acetate / dimethylformamide / 2 h / 0 °C

4: 90 percent / DBU / CH₂Cl₂ / -10 °C

5: 82 percent / BF₃*Et₂O / CH₂Cl₂ / 0.5 h / -60 °C

With pyridine; dmap; boron trifluoride diethyl etherate; hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: Acetylation / 3: Deacetylation / 4: Addition / 5: glycosylation;

DOI:10.1016/S0960-894X(00)00107-4

Reference yield:

((3R,4R,5R,6R)-2,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid 4-nitro-benzyl ester → 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-6-allyloxy-4-[(2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-2-yloxy]-3,5-dihydroxy-tetrahydro-pyran-2-ylmethyl ester (276241-34-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / pyridine; DMAP

2: 87 percent / hydrazine acetate / dimethylformamide / 2 h / 0 °C

3: 90 percent / DBU / CH₂Cl₂ / -10 °C

4: 82 percent / BF₃*Et₂O / CH₂Cl₂ / 0.5 h / -60 °C

With pyridine; dmap; boron trifluoride diethyl etherate; hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; N,N-dimethyl-formamide; 1: Acetylation / 2: Deacetylation / 3: Addition / 4: glycosylation;

DOI:10.1016/S0960-894X(00)00107-4

upstream raw materials:

allyl 6-O-pivaloyl-α-D-galactopyranoside

Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester

D-galactosamine

2-N-p-nitrobenzyloxycarbonyl-1,3,4,6-tetra-O-acetyl-D-galactosamine