(2R,3R,4R,5S)-4-Benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-carbaldehyde

Base Information

• Chemical Name: (2R,3R,4R,5S)-4-Benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-carbaldehyde
• CAS No.: 503609-54-9
• Molecular Formula: C₂₂H₂₆O₅
• Molecular Weight: 370.445

Synonyms:(2R,3R,4R,5S)-4-Benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-carbaldehyde

Chemical Property of (2R,3R,4R,5S)-4-Benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5S)-4-Benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-carbaldehyde

There total 8 articles about (2R,3R,4R,5S)-4-Benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-carbaldehyde 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: 95.0%

[(2R,3S,4R,5S)-4-Benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-methanol (503609-57-2) → (2R,3R,4R,5S)-4-Benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-carbaldehyde (503609-54-9)

Guidance literature:

With pyridine-SO₃ complex; dimethyl sulfoxide; In dichloromethane; at 0 ℃;

DOI:10.1021/ol034037a

Reference yield:

benzyl bromide (100-39-0) → (2R,3R,4R,5S)-4-Benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-carbaldehyde (503609-54-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

1.2: tetrabutylammonium iodide / 36 h / 20 °C

2.1: 10-camphorsulfonic acid / methanol; H₂O / 20 °C

3.1: 86 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

4.1: 93 percent / TfOH / diethyl ether

5.1: (DHQD)2PYR; K₃Fe(CN)6; aq. K₂CO₃ / K₂OsO₂(OH)4 / 2-methyl-propan-2-ol / 0 °C

6.1: NaOMe

7.1: 95 percent / SO₃*Pyr; DMSO / CH₂Cl₂ / 0 °C

With dmap; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; pyridine-SO₃ complex; trifluorormethanesulfonic acid; (1S)-10-camphorsulfonic acid; sodium methylate; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; potassium hexacyanoferrate(III); potassium dioxotetrahydroxoosmate(VI); In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; tert-butyl alcohol; 5.1: Sharpless asymmetric dihydroxylation / 7.1: Parikh-Doering oxidation;

DOI:10.1021/ol034037a

Reference yield:

(1R,2S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-methyl-but-3-en-1-ol (160797-23-9) → (2R,3R,4R,5S)-4-Benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-carbaldehyde (503609-54-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

1.2: tetrabutylammonium iodide / 36 h / 20 °C

2.1: 10-camphorsulfonic acid / methanol; H₂O / 20 °C

3.1: 86 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

4.1: 93 percent / TfOH / diethyl ether

5.1: (DHQD)2PYR; K₃Fe(CN)6; aq. K₂CO₃ / K₂OsO₂(OH)4 / 2-methyl-propan-2-ol / 0 °C

6.1: NaOMe

7.1: 95 percent / SO₃*Pyr; DMSO / CH₂Cl₂ / 0 °C

With dmap; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; pyridine-SO₃ complex; trifluorormethanesulfonic acid; (1S)-10-camphorsulfonic acid; sodium methylate; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; potassium hexacyanoferrate(III); potassium dioxotetrahydroxoosmate(VI); In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; tert-butyl alcohol; 5.1: Sharpless asymmetric dihydroxylation / 7.1: Parikh-Doering oxidation;

DOI:10.1021/ol034037a

upstream raw materials:

[(2R,3S,4R,5S)-4-Benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-methanol

benzyl bromide

(1R,2S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-methyl-but-3-en-1-ol

(S)-4-((1R,2S)-1-Benzyloxy-2-methyl-but-3-enyl)-2,2-dimethyl-[1,3]dioxolane

Downstream raw materials:

(S)-{2-[(4S,5S,6R)-6-(4-Benzyloxy-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-ylmethyl]-[1,3]dithian-2-yl}-[(2R,3S,4R,5S)-4-benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-methanol

(2R,3R,4R,5S)-2-{(S)-[(2R,4S,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(4-hydroxy-butyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-hydroxy-methyl}-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-4-ol

(2R,4S,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(4-hydroxy-butyl)-2-{(S)-hydroxy-[(2R,3R,4R,5S)-4-hydroxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-methyl}-5-methyl-tetrahydro-pyran-2-ol

(2R,4S,5R,6R)-6-(4-Benzyloxy-butyl)-2-{(S)-[(2R,3S,4R,5S)-4-benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-hydroxy-methyl}-5-methyl-tetrahydro-pyran-2,4-diol

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