(2S,4S,5S)-4-Acetoxy-5-acetylamino-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,4S,5S)-4-Acetoxy-5-acetylamino-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 149297-74-5
• Molecular Formula: C₃₉H₄₇NO₁₂
• Molecular Weight: 721.802
• Mol file: 149297-74-5.mol

Synonyms:

Chemical Property of (2S,4S,5S)-4-Acetoxy-5-acetylamino-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S,5S)-4-Acetoxy-5-acetylamino-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 14 articles about (2S,4S,5S)-4-Acetoxy-5-acetylamino-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl 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:

methyl-2,3,4-tri-O-benzyl-6-O-trifluoromethanesulfonyl-α-D-glucopyranoside (76679-47-5) → (2S,4S,5S)-4-Acetoxy-5-acetylamino-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (149297-74-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 1) NaH / 1) THF, -10 deg C, 2) r.t.

2: 81 percent / Dowex 50 WX₂ / methanol / 0 °C

3: 91 percent / imidazole / dimethylformamide

4: 1) Tf₂O, pyridine, 2) NaN₃ / 1) -30 deg C

5: 73 percent / aq. TFA / CH₂Cl₂

6: pyridine

7: 95 percent / DBU / CH₂Cl₂ / -78 °C

8: ethanol / 0 °C

9: 1) N-iodosuccinimide (NIS), 2) pyridine / 1) EtCN, -78 deg C

10: 1) NaNO₂, Ac₂O

11: Bu₃SnH / toluene / 12 h / 10 °C

With pyridine; 1H-imidazole; N-iodo-succinimide; sodium azide; trifluoromethylsulfonic anhydride; Dowex 50 WX₂; tri-n-butyl-tin hydride; acetic anhydride; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; sodium nitrite; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)60807-9

Reference yield:

methyl 3,4:5,6-di-O-isopropylidene-D-gluconate (114743-85-0) → (2S,4S,5S)-4-Acetoxy-5-acetylamino-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (149297-74-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 1) NaH / 1) THF, -10 deg C, 2) r.t.

2: 81 percent / Dowex 50 WX₂ / methanol / 0 °C

3: 91 percent / imidazole / dimethylformamide

4: 1) Tf₂O, pyridine, 2) NaN₃ / 1) -30 deg C

5: 73 percent / aq. TFA / CH₂Cl₂

6: pyridine

7: 95 percent / DBU / CH₂Cl₂ / -78 °C

8: ethanol / 0 °C

9: 1) N-iodosuccinimide (NIS), 2) pyridine / 1) EtCN, -78 deg C

10: 1) NaNO₂, Ac₂O

11: Bu₃SnH / toluene / 12 h / 10 °C

With pyridine; 1H-imidazole; N-iodo-succinimide; sodium azide; trifluoromethylsulfonic anhydride; Dowex 50 WX₂; tri-n-butyl-tin hydride; acetic anhydride; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; sodium nitrite; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)60807-9

Reference yield:

(R)-[(4S,5R)-5-((R)-1,2-Dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-acetic acid methyl ester → (2S,4S,5S)-4-Acetoxy-5-acetylamino-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (149297-74-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 91 percent / imidazole / dimethylformamide

2: 1) Tf₂O, pyridine, 2) NaN₃ / 1) -30 deg C

3: 73 percent / aq. TFA / CH₂Cl₂

4: pyridine

5: 95 percent / DBU / CH₂Cl₂ / -78 °C

6: ethanol / 0 °C

7: 1) N-iodosuccinimide (NIS), 2) pyridine / 1) EtCN, -78 deg C

8: 1) NaNO₂, Ac₂O

9: Bu₃SnH / toluene / 12 h / 10 °C

With pyridine; 1H-imidazole; N-iodo-succinimide; sodium azide; trifluoromethylsulfonic anhydride; tri-n-butyl-tin hydride; acetic anhydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; sodium nitrite; In ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)60807-9

upstream raw materials:

acetic anhydride

methyl-2,3,4-tri-O-benzyl-6-O-trifluoromethanesulfonyl-α-D-glucopyranoside

methyl 3,4:5,6-di-O-isopropylidene-D-gluconate

(R)-((4R,5S,4'R)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-acetic acid methyl ester