(3S,4S,5R)-4,5-Bis-benzyloxy-1-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-pentan-2-one

Base Information

• Chemical Name: (3S,4S,5R)-4,5-Bis-benzyloxy-1-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-pentan-2-one
• CAS No.: 115914-97-1
• Molecular Formula: C₅₂H₆₀O₁₁
• Molecular Weight: 861.042
• Mol file: 115914-97-1.mol

Synonyms:

Chemical Property of (3S,4S,5R)-4,5-Bis-benzyloxy-1-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-pentan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S,5R)-4,5-Bis-benzyloxy-1-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-pentan-2-one

There total 15 articles about (3S,4S,5R)-4,5-Bis-benzyloxy-1-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-pentan-2-one 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:

2-((3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-ethanol (138061-61-7) → (3S,4S,5R)-4,5-Bis-benzyloxy-1-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-pentan-2-one (115914-97-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / Et₃N / diethyl ether / 0 °C

2: 94 percent / NaI, NaHCO₃ / acetone

3: 95 percent / dimethylformamide / 110 °C

4: 1) n-BuLi / 1) THF, 0 deg C

5: 75 percent / N,N'-bis(mesitylmethyl)-(R,R')-1,2-diphenyl-1,2-diaminoethane / OsO₄ / CH₂Cl₂ / -80 °C

6: 1) NaH / 1) THF, 0 deg C

7: 1) (COCl)2, DMSO, 2) Et₃N

With n-butyllithium; oxalyl dichloride; 1,2-diphenyl-N,N'-bis[(2,4,6-trimethylphenyl)methyl]-1,2-diaminoethane; sodium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; sodium iodide; osmium(VIII) oxide; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00028a017

Reference yield:

(2S,3R,4R)-2,3-dibenzyloxy-4,5-isopropylidenedioxypentanal (106929-09-3) → (3S,4S,5R)-4,5-Bis-benzyloxy-1-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-pentan-2-one (115914-97-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) n-BuLi / 1) THF, 0 deg C

2: 75 percent / N,N'-bis(mesitylmethyl)-(R,R')-1,2-diphenyl-1,2-diaminoethane / OsO₄ / CH₂Cl₂ / -80 °C

3: 1) NaH / 1) THF, 0 deg C

4: 1) (COCl)2, DMSO, 2) Et₃N

With n-butyllithium; oxalyl dichloride; 1,2-diphenyl-N,N'-bis[(2,4,6-trimethylphenyl)methyl]-1,2-diaminoethane; sodium hydride; dimethyl sulfoxide; triethylamine; osmium(VIII) oxide; In dichloromethane;

DOI:10.1021/jo00028a017

Reference yield:

2,3-di-O-benzyl-4,5-O-isopropylidene-D-arabinitol (121964-07-6) → (3S,4S,5R)-4,5-Bis-benzyloxy-1-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-pentan-2-one (115914-97-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) (COCl)2, DMSO, 2) Et₃N

2: 1) n-BuLi / 1) THF, 0 deg C

3: 75 percent / N,N'-bis(mesitylmethyl)-(R,R')-1,2-diphenyl-1,2-diaminoethane / OsO₄ / CH₂Cl₂ / -80 °C

4: 1) NaH / 1) THF, 0 deg C

5: 1) (COCl)2, DMSO, 2) Et₃N

With n-butyllithium; oxalyl dichloride; 1,2-diphenyl-N,N'-bis[(2,4,6-trimethylphenyl)methyl]-1,2-diaminoethane; sodium hydride; dimethyl sulfoxide; triethylamine; osmium(VIII) oxide; In dichloromethane;

DOI:10.1021/jo00028a017

upstream raw materials:

p-Methoxybenzyl bromide

2-((3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-ethanol

(2S,3R,4R)-2,3-dibenzyloxy-4,5-isopropylidenedioxypentanal

2,3-di-O-benzyl-4,5-O-isopropylidene-D-arabinitol

Downstream raw materials:

C₅₅H₅₈⁽²⁾H₂O₉

C₅₂H₅₈⁽²⁾H₂O₁₁