(3S,4S,5R)-4,5-Bis-benzyloxy-1-((2S,3R,5R,6S)-5-benzyloxy-2-benzyloxymethyl-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-((2S,3R,5R,6S)-5-benzyloxy-2-benzyloxymethyl-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.: 138181-84-7
• Molecular Formula: C₅₃H₆₂O₁₁
• Molecular Weight: 875.069

Synonyms:(3S,4S,5R)-4,5-Bis-benzyloxy-1-((2S,3R,5R,6S)-5-benzyloxy-2-benzyloxymethyl-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 of (3S,4S,5R)-4,5-Bis-benzyloxy-1-((2S,3R,5R,6S)-5-benzyloxy-2-benzyloxymethyl-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:

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Safty Information:

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Technology Process of (3S,4S,5R)-4,5-Bis-benzyloxy-1-((2S,3R,5R,6S)-5-benzyloxy-2-benzyloxymethyl-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 27 articles about (3S,4S,5R)-4,5-Bis-benzyloxy-1-((2S,3R,5R,6S)-5-benzyloxy-2-benzyloxymethyl-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:

benzyl bromide (100-39-0) → (3S,4S,5R)-4,5-Bis-benzyloxy-1-((2S,3R,5R,6S)-5-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-pentan-2-one (138181-84-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) NaH / 1) THF, DMF, 2) 0 deg C, 5 h

2: 56 percent / N,N'-bis(mesitylmethyl)-(R,R')-1,2-diphenyl-1,2-diaminoethane / OsO₄ / CH₂Cl₂ / -80 °C

3: PPTS / benzene / 80 °C

4: 1) NaBH₃CN, 3 Angstroem molecular sieves, 2) CF₃COOH / 1) DMF, 2) DMF, 0 deg C

5: 1) (COCl)2, DMSO, 2) Et₃N

With oxalyl dichloride; 1,2-diphenyl-N,N'-bis[(2,4,6-trimethylphenyl)methyl]-1,2-diaminoethane; 3 A molecular sieve; pyridinium p-toluenesulfonate; sodium hydride; sodium cyanoborohydride; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; osmium(VIII) oxide; In dichloromethane; benzene;

DOI:10.1021/jo00028a017

Reference yield:

Methyl 2,6-di-O-benzyl-3-deoxy-α-D-ribo-hexopyranoside (117371-67-2) → (3S,4S,5R)-4,5-Bis-benzyloxy-1-((2S,3R,5R,6S)-5-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-pentan-2-one (138181-84-7)

Guidance literature:

Multi-step reaction with 15 steps

1: 1) (COCl)2, DMSO, 2) Et₃N

2: 96 percent / t-BuOK / tetrahydrofuran; dimethylformamide / 0 °C

3: H₂ / Pd / C / ethanol

4: 81 percent / LiAlH₄ / diethyl ether / 0 °C

5: 1) (COCl)2, DMSO, 2) Et₃N

6: 1) PPh₃ / 1) CH₂Cl₂, 30 min., 2) CH₂Cl₂, 0 deg C, 2 h

7: 83 percent / BuLi / tetrahydrofuran / 1 h / -78 °C

8: 75 percent / I₂, morpholine / benzene / 3 h / 50 °C

9: 43 percent / CrCl₂ + 0.2percent NiCl₂ / tetrahydrofuran / 12 h

10: H₂ / Lindlar catalyst / methanol / 3 h

11: 1) NaH / 1) THF, DMF, 2) 0 deg C, 5 h

12: 56 percent / N,N'-bis(mesitylmethyl)-(R,R')-1,2-diphenyl-1,2-diaminoethane / OsO₄ / CH₂Cl₂ / -80 °C

13: PPTS / benzene / 80 °C

14: 1) NaBH₃CN, 3 Angstroem molecular sieves, 2) CF₃COOH / 1) DMF, 2) DMF, 0 deg C

15: 1) (COCl)2, DMSO, 2) Et₃N

With morpholine; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 1,2-diphenyl-N,N'-bis[(2,4,6-trimethylphenyl)methyl]-1,2-diaminoethane; 3 A molecular sieve; potassium tert-butylate; hydrogen; iodine; pyridinium p-toluenesulfonate; sodium hydride; sodium cyanoborohydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; Lindlar's catalyst; osmium(VIII) oxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene;

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-((2S,3R,5R,6S)-5-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-pentan-2-one (138181-84-7)

Guidance literature:

Multi-step reaction with 10 steps

1: MCPBA / CH₂Cl₂ / 3 h / phosphate buffer (pH 7)

2: LiAlH₄ / diethyl ether / 1 h / 0 °C

3: 1) (COCl)2, DMSO, 2) Et₃N

4: 43 percent / CrCl₂ + 0.2percent NiCl₂ / tetrahydrofuran / 12 h

5: H₂ / Lindlar catalyst / methanol / 3 h

6: 1) NaH / 1) THF, DMF, 2) 0 deg C, 5 h

7: 56 percent / N,N'-bis(mesitylmethyl)-(R,R')-1,2-diphenyl-1,2-diaminoethane / OsO₄ / CH₂Cl₂ / -80 °C

8: PPTS / benzene / 80 °C

9: 1) NaBH₃CN, 3 Angstroem molecular sieves, 2) CF₃COOH / 1) DMF, 2) DMF, 0 deg C

10: 1) (COCl)2, DMSO, 2) Et₃N

With lithium aluminium tetrahydride; oxalyl dichloride; 1,2-diphenyl-N,N'-bis[(2,4,6-trimethylphenyl)methyl]-1,2-diaminoethane; 3 A molecular sieve; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; sodium cyanoborohydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; Lindlar's catalyst; osmium(VIII) oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene;

DOI:10.1021/jo00028a017

upstream raw materials:

benzyl bromide

methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

(R)-2-(benzyloxy)-2-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde

Methyl 2,6-di-O-benzyl-3-deoxy-α-D-ribo-hexopyranoside

Downstream raw materials:

C₅₆H₆₀⁽²⁾H₂O₉

C₅₃H₆₀⁽²⁾H₂O₁₁

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