(3R,4R,5R,6S)-4-Benzyloxy-6-[(1R,2R,3S,4S)-2,4-bis-benzyloxy-1-methoxymethoxymethyl-3-methyl-4-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-butyl]-3,5-dimethyl-tetrahydro-pyran-2,3-diol

Base Information

• Chemical Name: (3R,4R,5R,6S)-4-Benzyloxy-6-[(1R,2R,3S,4S)-2,4-bis-benzyloxy-1-methoxymethoxymethyl-3-methyl-4-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-butyl]-3,5-dimethyl-tetrahydro-pyran-2,3-diol
• CAS No.: 129163-53-7
• Molecular Formula: C₄₂H₅₈O₁₀
• Molecular Weight: 722.917

Synonyms:

Chemical Property of (3R,4R,5R,6S)-4-Benzyloxy-6-[(1R,2R,3S,4S)-2,4-bis-benzyloxy-1-methoxymethoxymethyl-3-methyl-4-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-butyl]-3,5-dimethyl-tetrahydro-pyran-2,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5R,6S)-4-Benzyloxy-6-[(1R,2R,3S,4S)-2,4-bis-benzyloxy-1-methoxymethoxymethyl-3-methyl-4-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-butyl]-3,5-dimethyl-tetrahydro-pyran-2,3-diol

There total 20 articles about (3R,4R,5R,6S)-4-Benzyloxy-6-[(1R,2R,3S,4S)-2,4-bis-benzyloxy-1-methoxymethoxymethyl-3-methyl-4-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-butyl]-3,5-dimethyl-tetrahydro-pyran-2,3-diol 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:

(3R,4S,5R,6S,7R,8S,9S)-3,7,9-Tris-benzyloxy-6-methoxymethoxymethyl-2,4,8-trimethyl-9-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-non-1-en-5-ol (123506-10-5) → (3R,4R,5R,6S)-4-Benzyloxy-6-[(1R,2R,3S,4S)-2,4-bis-benzyloxy-1-methoxymethoxymethyl-3-methyl-4-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-butyl]-3,5-dimethyl-tetrahydro-pyran-2,3-diol (129163-53-7,129214-44-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) ozone, 2.) dimethylsulfide / 1.) dichloromethan, methanol, -78 deg C, 10 min, 2.) 0 deg C, 1 h

2: tetrahydrofuran / -30 °C

3: 1.) ozone, 2.) dimethylsulfide / 1.) dichloromethane, methanol, -78 deg C, 10 min, 2.) 0 deg C, 1 h

With dimethylsulfide; ozone; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)97592-1

Reference yield:

Tri-O-benzyl-1,2-O-carbonyl-4,6,8,10,11-pentadeoxy-6-(1''-methoxymethoxymethyl)-2,4,8,10-tetra-C-methyl-L-altro-L-galacto-10-eno-undecitol (123506-09-2) → (3R,4R,5R,6S)-4-Benzyloxy-6-[(1R,2R,3S,4S)-2,4-bis-benzyloxy-1-methoxymethoxymethyl-3-methyl-4-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-butyl]-3,5-dimethyl-tetrahydro-pyran-2,3-diol (129163-53-7,129214-44-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) methyllithium, 2.) dicamphorsulfonic acid / 1.) ether, -78 deg C --> -20 deg C, 2.) dichloromethane, room temperature, 20 min

2: 1.) ozone, 2.) dimethylsulfide / 1.) dichloromethan, methanol, -78 deg C, 10 min, 2.) 0 deg C, 1 h

3: tetrahydrofuran / -30 °C

4: 1.) ozone, 2.) dimethylsulfide / 1.) dichloromethane, methanol, -78 deg C, 10 min, 2.) 0 deg C, 1 h

With dimethylsulfide; dicamphorsulfonic acid; methyllithium; ozone; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)97592-1

Reference yield:

(3R,4S,5R,6S,7R,8S,9S)-3,7,9-Tris-benzyloxy-5-hydroxy-6-methoxymethoxymethyl-4,8-dimethyl-9-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-nonan-2-one → (3R,4R,5R,6S)-4-Benzyloxy-6-[(1R,2R,3S,4S)-2,4-bis-benzyloxy-1-methoxymethoxymethyl-3-methyl-4-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-butyl]-3,5-dimethyl-tetrahydro-pyran-2,3-diol (129163-53-7,129214-44-4)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / -30 °C

2: 1.) ozone, 2.) dimethylsulfide / 1.) dichloromethane, methanol, -78 deg C, 10 min, 2.) 0 deg C, 1 h

With dimethylsulfide; ozone; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)97592-1

upstream raw materials:

(3R,4S,5R,6S,7R,8S,9S)-3,7,9-Tris-benzyloxy-6-methoxymethoxymethyl-2,4,8-trimethyl-9-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-non-1-en-5-ol

Tri-O-benzyl-1,2-O-carbonyl-4,6,8,10,11-pentadeoxy-6-(1''-methoxymethoxymethyl)-2,4,8,10-tetra-C-methyl-L-altro-L-galacto-10-eno-undecitol

(2S,3S,4S,5R,6R)-3,5-Bis-benzyloxy-6-((2R,3S,4R,5S)-4-benzyloxy-5-bromomethyl-3,5-dimethyl-tetrahydro-furan-2-yl)-7-methoxymethoxy-2-methyl-4-vinyl-heptane-1,2-diol

{(2S,3R,4S,5S)-3-Benzyloxy-4-[(1S,2R)-1-benzyloxy-2-((2R,3S,4R,5S)-4-benzyloxy-5-bromomethyl-3,5-dimethyl-tetrahydro-furan-2-yl)-3-methoxymethoxy-propyl]-5-iodomethyl-2-methyl-tetrahydro-furan-2-yl}-methanol

Downstream raw materials:

(3R,4R,5R,6S)-4-Benzyloxy-6-[(1R,2R,3S,4S)-2,4-bis-benzyloxy-1-methoxymethoxymethyl-3-methyl-4-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-butyl]-3-hydroxy-3,5-dimethyl-tetrahydro-pyran-2-one

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