(2R,4R,5R,6S)-3-Chloro-4,6-dimethoxy-5-methyl-2-trityloxymethyl-tetrahydro-pyran

Base Information

• Chemical Name: (2R,4R,5R,6S)-3-Chloro-4,6-dimethoxy-5-methyl-2-trityloxymethyl-tetrahydro-pyran
• CAS No.: 82707-17-3
• Molecular Formula: C₂₈H₃₁ClO₄
• Molecular Weight: 467.005
• Mol file: 82707-17-3.mol

Synonyms:(2R,4R,5R,6S)-3-Chloro-4,6-dimethoxy-5-methyl-2-trityloxymethyl-tetrahydro-pyran

Chemical Property of (2R,4R,5R,6S)-3-Chloro-4,6-dimethoxy-5-methyl-2-trityloxymethyl-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4R,5R,6S)-3-Chloro-4,6-dimethoxy-5-methyl-2-trityloxymethyl-tetrahydro-pyran

There total 14 articles about (2R,4R,5R,6S)-3-Chloro-4,6-dimethoxy-5-methyl-2-trityloxymethyl-tetrahydro-pyran 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: 75.0%

(2R,4R,5R,6S)-4,6-Dimethoxy-5-methyl-2-trityloxymethyl-tetrahydro-pyran-3-ol (64526-83-6,92232-36-5) → (2R,4R,5R,6S)-3-Chloro-4,6-dimethoxy-5-methyl-2-trityloxymethyl-tetrahydro-pyran (82707-17-3)

Guidance literature:

With pyridine; thionyl chloride; for 18h; -75 deg C -> 25 deg C;

DOI:10.1021/ja00386a076

Reference yield:

methyl 2-deoxy-2-C-methyl-3-O-methyl-6-O-triphenylmethyl-α-D-allopyranoside (64526-83-6) → (2R,4R,5R,6S)-3-Chloro-4,6-dimethoxy-5-methyl-2-trityloxymethyl-tetrahydro-pyran (82707-17-3)

Guidance literature:

Multi-step reaction with 4 steps

1: ethyldimethylaminopropyl carbodiimide, HCl / dimethylsulfoxide

2: 85 percent / NaOMe / methanol

3: 97 percent / NaBH₄ / methanol

4: 75 percent / SOCl₂, pyridine / 18 h / -75 deg C -> 25 deg C

With pyridine; hydrogenchloride; sodium tetrahydroborate; thionyl chloride; sodium methylate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In methanol; dimethyl sulfoxide;

DOI:10.1021/ja00386a076

Reference yield:

methyl 2-deoxy-2-C-methyl-3-O-methyl-6-O-triphenylmethyl-α-D-xylo-hexapyranosid-4-ulose (64526-85-8) → (2R,4R,5R,6S)-3-Chloro-4,6-dimethoxy-5-methyl-2-trityloxymethyl-tetrahydro-pyran (82707-17-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / NaBH₄ / methanol

2: 75 percent / SOCl₂, pyridine / 18 h / -75 deg C -> 25 deg C

With pyridine; sodium tetrahydroborate; thionyl chloride; In methanol;

DOI:10.1021/ja00386a076

upstream raw materials:

methyl 2-deoxy-2-C-methyl-3-O-methyl-6-O-triphenylmethyl-α-D-glucopyranoside

methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altro-pyranoside

Methyl 4,6-O-Benzylidene-2-deoxy-2-C-methyl-α-D-allopyranoside

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-4,6-dimethoxy-5-methyl-tetrahydro-pyran-3-ol

Downstream raw materials:

methyl 2,4-dideoxy-2-C-methyl-3-O-methyl-6-O-triphenylmethyl-α-D-xylo-hexopyranoside

(2S,3S,4R,8S,9S)-3-Benzyloxy-10-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-7-hydroxy-9-methoxy-2,4,6,8-tetramethyl-1-trityloxy-decan-5-one

(2S,3S,6S,7S,8S,9S)-8-Benzyloxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-3,5,7,9-tetramethyl-10-trityloxy-decane-4,6-diol

(2S,3S,4R,6S,7R,8S,9S)-3-Benzyloxy-10-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-7-hydroxy-9-methoxy-2,4,6,8-tetramethyl-1-trityloxy-decan-5-one