Carbonic acid (2R,3S,4R,5R)-2-benzyloxymethoxymethyl-6-bromo-3-(diphenoxy-phosphoryloxy)-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester 2,2,2-trichloro-1,1-dimethyl-ethyl ester

Base Information

• Chemical Name: Carbonic acid (2R,3S,4R,5R)-2-benzyloxymethoxymethyl-6-bromo-3-(diphenoxy-phosphoryloxy)-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester 2,2,2-trichloro-1,1-dimethyl-ethyl ester
• CAS No.: 155711-39-0
• Molecular Formula: C₃₄H₃₅BrCl₆NO₁₂P
• Molecular Weight: 973.247

Synonyms:

Chemical Property of Carbonic acid (2R,3S,4R,5R)-2-benzyloxymethoxymethyl-6-bromo-3-(diphenoxy-phosphoryloxy)-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester 2,2,2-trichloro-1,1-dimethyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Carbonic acid (2R,3S,4R,5R)-2-benzyloxymethoxymethyl-6-bromo-3-(diphenoxy-phosphoryloxy)-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester 2,2,2-trichloro-1,1-dimethyl-ethyl ester

There total 6 articles about Carbonic acid (2R,3S,4R,5R)-2-benzyloxymethoxymethyl-6-bromo-3-(diphenoxy-phosphoryloxy)-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester 2,2,2-trichloro-1,1-dimethyl-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:

Carbonic acid (2R,3S,4R,5R)-2-benzyloxymethoxymethyl-3-(diphenoxy-phosphoryloxy)-6-hydroxy-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester 2,2,2-trichloro-1,1-dimethyl-ethyl ester → Carbonic acid (2R,3S,4R,5R)-2-benzyloxymethoxymethyl-6-bromo-3-(diphenoxy-phosphoryloxy)-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester 2,2,2-trichloro-1,1-dimethyl-ethyl ester (155711-39-0)

Guidance literature:

With dibromo sulfoxide; N,N-dimethyl-formamide; In dichloromethane; at 0 - 5 ℃; for 2h;

DOI:10.1248/cpb.41.1879

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → Carbonic acid (2R,3S,4R,5R)-2-benzyloxymethoxymethyl-6-bromo-3-(diphenoxy-phosphoryloxy)-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester 2,2,2-trichloro-1,1-dimethyl-ethyl ester (155711-39-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 66 percent / 1,1,3,3-tetramethylurea / CH₂Cl₂ / 20 h / Ambient temperature

2: 89 percent / pyridine, DMAP / CH₂Cl₂ / 20 h / Ambient temperature

3: 1.) 2)2>PF₆, H₂, 2.) iodine, pyridine / 1.) THF, 50 deg C, 2 h, 2.) THF, H₂O, RT, 15 min

4: thionyl chloride, DMF / CH₂Cl₂ / 5 h / Ambient temperature

With pyridine; dmap; thionyl chloride; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; hydrogen; iodine; N,N-dimethyl-formamide; tetramethylurea; In dichloromethane;

DOI:10.1248/cpb.44.2268

Reference yield:

Allyl 2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (134040-52-1) → Carbonic acid (2R,3S,4R,5R)-2-benzyloxymethoxymethyl-6-bromo-3-(diphenoxy-phosphoryloxy)-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester 2,2,2-trichloro-1,1-dimethyl-ethyl ester (155711-39-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 66 percent / 1,1,3,3-tetramethylurea / CH₂Cl₂ / 20 h / Ambient temperature

2: 89 percent / pyridine, DMAP / CH₂Cl₂ / 20 h / Ambient temperature

3: 1.) 2)2>PF₆, H₂, 2.) iodine, pyridine / 1.) THF, 50 deg C, 2 h, 2.) THF, H₂O, RT, 15 min

4: thionyl chloride, DMF / CH₂Cl₂ / 5 h / Ambient temperature

With pyridine; dmap; thionyl chloride; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; hydrogen; iodine; N,N-dimethyl-formamide; tetramethylurea; In dichloromethane;

DOI:10.1248/cpb.44.2268

upstream raw materials:

Carbonic acid (2R,3S,4R,5R,6S)-2-benzyloxymethoxymethyl-3-(diphenoxy-phosphoryloxy)-6-hydroxy-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester 2,2,2-trichloro-1,1-dimethyl-ethyl ester

Benzyloxymethyl chloride

Allyl 2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

allyl 6-O-benzyloxymethyl-2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Downstream raw materials:

(S)-3-[(2R,3R,4R,5S,6R)-3-Amino-6-benzyloxymethoxymethyl-5-(diphenoxy-phosphoryloxy)-4-hydroxy-tetrahydro-pyran-2-yloxy]-2-tetradecanoylamino-propionic acid benzyl ester

(S)-3-[(2R,3R,4R,5S,6R)-6-Benzyloxymethoxymethyl-5-(diphenoxy-phosphoryloxy)-4-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonyloxy)-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-2-tetradecanoylamino-propionic acid benzyl ester

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