(2S,3R,6S)-6-((2S,5S)-5-Benzyloxymethyl-tetrahydro-furan-2-yl)-2,3-dihydroxy-6-methoxymethoxy-hexanoic acid ethyl ester

Base Information

• Chemical Name: (2S,3R,6S)-6-((2S,5S)-5-Benzyloxymethyl-tetrahydro-furan-2-yl)-2,3-dihydroxy-6-methoxymethoxy-hexanoic acid ethyl ester
• CAS No.: 228853-22-3
• Molecular Formula: C₂₂H₃₄O₈
• Molecular Weight: 426.507

Synonyms:(2S,3R,6S)-6-((2S,5S)-5-Benzyloxymethyl-tetrahydro-furan-2-yl)-2,3-dihydroxy-6-methoxymethoxy-hexanoic acid ethyl ester

Chemical Property of (2S,3R,6S)-6-((2S,5S)-5-Benzyloxymethyl-tetrahydro-furan-2-yl)-2,3-dihydroxy-6-methoxymethoxy-hexanoic acid ethyl ester

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,6S)-6-((2S,5S)-5-Benzyloxymethyl-tetrahydro-furan-2-yl)-2,3-dihydroxy-6-methoxymethoxy-hexanoic acid ethyl ester

There total 7 articles about (2S,3R,6S)-6-((2S,5S)-5-Benzyloxymethyl-tetrahydro-furan-2-yl)-2,3-dihydroxy-6-methoxymethoxy-hexanoic acid ethyl 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: 97.0%

(E)-(S)-6-((2S,5S)-5-Benzyloxymethyl-tetrahydro-furan-2-yl)-6-methoxymethoxy-hex-2-enoic acid ethyl ester (228853-21-2) → (2S,3R,6S)-6-((2S,5S)-5-Benzyloxymethyl-tetrahydro-furan-2-yl)-2,3-dihydroxy-6-methoxymethoxy-hexanoic acid ethyl ester (228853-22-3)

Guidance literature:

With potassium dioxotetrahydroxoosmate(VI); potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In tert-butyl alcohol; at 0 ℃;

DOI:10.1016/S0957-4166(99)00039-7

Reference yield:

(5S,6S)-5,6-dihydroxydeca-1,9-diene (221467-95-4) → (2S,3R,6S)-6-((2S,5S)-5-Benzyloxymethyl-tetrahydro-furan-2-yl)-2,3-dihydroxy-6-methoxymethoxy-hexanoic acid ethyl ester (228853-22-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 67 percent / NaH / tetrahydrofuran

2: 74 percent / Co(modp)2, TBHP, O₂ / propan-2-ol

3: 98 percent / NaH / tetrahydrofuran

4: K₃Fe(CN)6, aq. K₂CO₃, K₂OsO₂(OH)4 / 2-methyl-propan-2-ol / Ambient temperature

5: aq. NaIO₄ / tetrahydrofuran

6: benzene

7: 97 percent / K₃Fe(CN)6, aq. K₂CO₃, (DHQD)2PHAL, K₂OsO₂(OH)4 / 2-methyl-propan-2-ol / 0 °C

With tert.-butylhydroperoxide; sodium periodate; potassium dioxotetrahydroxoosmate(VI); Co(modp)2; oxygen; sodium hydride; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In tetrahydrofuran; isopropyl alcohol; tert-butyl alcohol; benzene;

DOI:10.1016/S0957-4166(99)00039-7

Reference yield:

(5S,6S)-6-methoxymethoxy-1,9-decadiene-5-ol (228853-17-6) → (2S,3R,6S)-6-((2S,5S)-5-Benzyloxymethyl-tetrahydro-furan-2-yl)-2,3-dihydroxy-6-methoxymethoxy-hexanoic acid ethyl ester (228853-22-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 74 percent / Co(modp)2, TBHP, O₂ / propan-2-ol

2: 98 percent / NaH / tetrahydrofuran

3: K₃Fe(CN)6, aq. K₂CO₃, K₂OsO₂(OH)4 / 2-methyl-propan-2-ol / Ambient temperature

4: aq. NaIO₄ / tetrahydrofuran

5: benzene

6: 97 percent / K₃Fe(CN)6, aq. K₂CO₃, (DHQD)2PHAL, K₂OsO₂(OH)4 / 2-methyl-propan-2-ol / 0 °C

With tert.-butylhydroperoxide; sodium periodate; potassium dioxotetrahydroxoosmate(VI); Co(modp)2; oxygen; sodium hydride; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In tetrahydrofuran; isopropyl alcohol; tert-butyl alcohol; benzene;

DOI:10.1016/S0957-4166(99)00039-7

upstream raw materials:

(E)-(S)-6-((2S,5S)-5-Benzyloxymethyl-tetrahydro-furan-2-yl)-6-methoxymethoxy-hex-2-enoic acid ethyl ester

(5S,6S)-5,6-dihydroxydeca-1,9-diene

(5S,6S)-6-methoxymethoxy-1,9-decadiene-5-ol

(2S,5S,6S)-2,5-epoxy-6-methoxymethoxy-9-decanene-1-ol

Downstream raw materials:

(4S,5R)-5-[(S)-3-((2S,5S)-5-Benzyloxymethyl-tetrahydro-furan-2-yl)-3-methoxymethoxy-propyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester

(4S,5R)-5-[(S)-3-((2S,5S)-5-Benzyloxymethyl-tetrahydro-furan-2-yl)-3-methoxymethoxy-propyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

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