(2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-(4-nitro-benzyloxymethyl)-6-((S)-1-oxiranylmethoxy)-tetrahydro-pyran

Base Information

• Chemical Name: (2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-(4-nitro-benzyloxymethyl)-6-((S)-1-oxiranylmethoxy)-tetrahydro-pyran
• CAS No.: 176911-83-4
• Molecular Formula: C₃₇H₃₉NO₉
• Molecular Weight: 641.718
• Mol file: 176911-83-4.mol

Synonyms:(2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-(4-nitro-benzyloxymethyl)-6-((S)-1-oxiranylmethoxy)-tetrahydro-pyran

Chemical Property of (2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-(4-nitro-benzyloxymethyl)-6-((S)-1-oxiranylmethoxy)-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-(4-nitro-benzyloxymethyl)-6-((S)-1-oxiranylmethoxy)-tetrahydro-pyran

There total 1 articles about (2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-(4-nitro-benzyloxymethyl)-6-((S)-1-oxiranylmethoxy)-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: 85.0%

2,3,4-tri-O-benzyl-6-O-p-nitrobenzoyl-α-D-glucopyranosyl bromide (39483-53-9) + (S)-oxiranemethanol (60456-23-7) → (2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-(4-nitro-benzyloxymethyl)-6-((S)-1-oxiranylmethoxy)-tetrahydro-pyran (176911-83-4)

Guidance literature:

With tetramethylurea; In dichloromethane;

DOI:10.1016/S0040-4039(00)73526-X

Reference yield:

(2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-(4-nitro-benzyloxymethyl)-6-((S)-1-oxiranylmethoxy)-tetrahydro-pyran (176911-83-4) → [(2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-6-((S)-1-oxiranylmethoxy)-tetrahydro-pyran-2-yl]-methanol

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1016/S0040-4039(00)73526-X

Reference yield:

(2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-(4-nitro-benzyloxymethyl)-6-((S)-1-oxiranylmethoxy)-tetrahydro-pyran (176911-83-4) → Hexadecanoic acid (S)-2-hydroxy-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester (158227-69-1)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium methoxide / methanol

2: 70 percent / dimethylformamide

With sodium methylate; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)73526-X

upstream raw materials:

2,3,4-tri-O-benzyl-6-O-p-nitrobenzoyl-α-D-glucopyranosyl bromide

(S)-oxiranemethanol

Downstream raw materials:

Hexadecanoic acid (S)-2-hydroxy-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester

Hexadecanoic acid (S)-1-hexadecanoyloxymethyl-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethyl ester

Hexadecanoic acid (S)-1-hexadecanoyloxymethyl-2-[(2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yloxy]-ethyl ester

Hexadecanoic acid (S)-1-hexadecanoyloxymethyl-2-{(2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-[(2-bromo-ethoxy)-hydroxy-phosphoryloxymethyl]-tetrahydro-pyran-2-yloxy}-ethyl ester